Retipolides - unusual spiromacrolactones from the mushrooms Retiboletus retipes and R. ornatipes

Publikation: Beiträge in ZeitschriftenZeitschriftenaufsätzeForschung

Standard

Retipolides - unusual spiromacrolactones from the mushrooms Retiboletus retipes and R. ornatipes. / Justus, Karl; Herrmann, Rupert; Klamann, Jörg-Dieter et al.
in: European Journal of Organic Chemistry, Jahrgang 2007, Nr. 33, 01.11.2007, S. 5560-5572.

Publikation: Beiträge in ZeitschriftenZeitschriftenaufsätzeForschung

Harvard

Justus, K, Herrmann, R, Klamann, J-D, Gruber, G, Hellwig, V, Ingerl, A, Polborn, K, Steffan, B & Steglich, W 2007, 'Retipolides - unusual spiromacrolactones from the mushrooms Retiboletus retipes and R. ornatipes', European Journal of Organic Chemistry, Jg. 2007, Nr. 33, S. 5560-5572. https://doi.org/10.1002/ejoc.200700579

APA

Justus, K., Herrmann, R., Klamann, J.-D., Gruber, G., Hellwig, V., Ingerl, A., Polborn, K., Steffan, B., & Steglich, W. (2007). Retipolides - unusual spiromacrolactones from the mushrooms Retiboletus retipes and R. ornatipes. European Journal of Organic Chemistry, 2007(33), 5560-5572. https://doi.org/10.1002/ejoc.200700579

Vancouver

Justus K, Herrmann R, Klamann JD, Gruber G, Hellwig V, Ingerl A et al. Retipolides - unusual spiromacrolactones from the mushrooms Retiboletus retipes and R. ornatipes. European Journal of Organic Chemistry. 2007 Nov 1;2007(33):5560-5572. doi: 10.1002/ejoc.200700579

Bibtex

@article{07400a3407ac489aa6bfc96175620934,
title = "Retipolides - unusual spiromacrolactones from the mushrooms Retiboletus retipes and R. ornatipes",
abstract = "Mushrooms of the genus Retiboletus contain the retipolides A-D (1, 6-8), unusual 14-membered spiromacrolides with a biphenyl ether linkage. The structures of these metabolites suggested a biogenetic sequence starting from retipolide E (16), which could furnish the unique 2(3H)-oxepinone unit of retipolide C (7) via an oxidative enlargement of the 4-hydroxyphenyl ring. A subsequent O/C-acyl shift would then lead to the cyclopenta[c]pyran system of retipolide A (1). The proposed precursor 16 was synthesized and subsequently detected in the fungal extract in addition to the probable biosynthetic intermediates butyrolactone II (13), tyrosol (14), and secoretipolide E (15). The structural elucidation of retipolide A (1) was accomplished after transformation into a methoxyfulvene derivative 2a, and the absolute (R) configuration of 1 was assigned by a single-crystal X-ray analysis of the corresponding (S)-sec-butoxyfulvene analogue 2b. Some samples of R. retipes/ornatipes contained isoretipolide A (9), an isomer of 1 with a highly strained 12-membered lactone ring incorporating two C,C-coupled 4-hydroxyphenyl units. A comparison of the CD spectrum of retipolide A (1) with those of the other retipolides and isoretipolide A (9) indicates that all of these macrolides possess R configuration.",
keywords = "Chemistry, Basidiomycetes, Macrolactones, Natural products, Oxepinones, Retipolides, Spiro compounds",
author = "Karl Justus and Rupert Herrmann and J{\"o}rg-Dieter Klamann and Gertraud Gruber and Veronika Hellwig and Andrea Ingerl and Kurt Polborn and Bert Steffan and Wolfgang Steglich",
year = "2007",
month = nov,
day = "1",
doi = "10.1002/ejoc.200700579",
language = "English",
volume = "2007",
pages = "5560--5572",
journal = "European Journal of Organic Chemistry",
issn = "1434-193X",
publisher = "Wiley-VCH Verlag",
number = "33",

}

RIS

TY - JOUR

T1 - Retipolides - unusual spiromacrolactones from the mushrooms Retiboletus retipes and R. ornatipes

AU - Justus, Karl

AU - Herrmann, Rupert

AU - Klamann, Jörg-Dieter

AU - Gruber, Gertraud

AU - Hellwig, Veronika

AU - Ingerl, Andrea

AU - Polborn, Kurt

AU - Steffan, Bert

AU - Steglich, Wolfgang

PY - 2007/11/1

Y1 - 2007/11/1

N2 - Mushrooms of the genus Retiboletus contain the retipolides A-D (1, 6-8), unusual 14-membered spiromacrolides with a biphenyl ether linkage. The structures of these metabolites suggested a biogenetic sequence starting from retipolide E (16), which could furnish the unique 2(3H)-oxepinone unit of retipolide C (7) via an oxidative enlargement of the 4-hydroxyphenyl ring. A subsequent O/C-acyl shift would then lead to the cyclopenta[c]pyran system of retipolide A (1). The proposed precursor 16 was synthesized and subsequently detected in the fungal extract in addition to the probable biosynthetic intermediates butyrolactone II (13), tyrosol (14), and secoretipolide E (15). The structural elucidation of retipolide A (1) was accomplished after transformation into a methoxyfulvene derivative 2a, and the absolute (R) configuration of 1 was assigned by a single-crystal X-ray analysis of the corresponding (S)-sec-butoxyfulvene analogue 2b. Some samples of R. retipes/ornatipes contained isoretipolide A (9), an isomer of 1 with a highly strained 12-membered lactone ring incorporating two C,C-coupled 4-hydroxyphenyl units. A comparison of the CD spectrum of retipolide A (1) with those of the other retipolides and isoretipolide A (9) indicates that all of these macrolides possess R configuration.

AB - Mushrooms of the genus Retiboletus contain the retipolides A-D (1, 6-8), unusual 14-membered spiromacrolides with a biphenyl ether linkage. The structures of these metabolites suggested a biogenetic sequence starting from retipolide E (16), which could furnish the unique 2(3H)-oxepinone unit of retipolide C (7) via an oxidative enlargement of the 4-hydroxyphenyl ring. A subsequent O/C-acyl shift would then lead to the cyclopenta[c]pyran system of retipolide A (1). The proposed precursor 16 was synthesized and subsequently detected in the fungal extract in addition to the probable biosynthetic intermediates butyrolactone II (13), tyrosol (14), and secoretipolide E (15). The structural elucidation of retipolide A (1) was accomplished after transformation into a methoxyfulvene derivative 2a, and the absolute (R) configuration of 1 was assigned by a single-crystal X-ray analysis of the corresponding (S)-sec-butoxyfulvene analogue 2b. Some samples of R. retipes/ornatipes contained isoretipolide A (9), an isomer of 1 with a highly strained 12-membered lactone ring incorporating two C,C-coupled 4-hydroxyphenyl units. A comparison of the CD spectrum of retipolide A (1) with those of the other retipolides and isoretipolide A (9) indicates that all of these macrolides possess R configuration.

KW - Chemistry

KW - Basidiomycetes

KW - Macrolactones

KW - Natural products

KW - Oxepinones

KW - Retipolides

KW - Spiro compounds

UR - http://www.scopus.com/inward/record.url?scp=36348950256&partnerID=8YFLogxK

UR - https://www.mendeley.com/catalogue/b123d300-9560-3841-aa23-32427ef229fc/

U2 - 10.1002/ejoc.200700579

DO - 10.1002/ejoc.200700579

M3 - Journal articles

VL - 2007

SP - 5560

EP - 5572

JO - European Journal of Organic Chemistry

JF - European Journal of Organic Chemistry

SN - 1434-193X

IS - 33

ER -

DOI