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Retipolides – Unusual Spiromacrolactones from the Mushrooms Retiboletus retipes and R. ornatipes by Karl Justus; Rupert Herrmann; Jörg‐Dieter Klamann; Gertraud Gruber; Veronika Hellwig; Andrea Ingerl; Kurt Polborn; Bert Steffan; Wolfgang Steglich is a Chemistry article available to read on EtoBox.

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## 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(3__H__)‐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 incorpora

Who reads Retipolides – Unusual Spiromacrolactones from the Mushrooms Retiboletus retipes and R. ornatipes?

Author

Karl Justus; Rupert Herrmann; Jörg‐Dieter Klamann; Gertraud Gruber; Veronika Hellwig; Andrea Ingerl; Kurt Polborn; Bert Steffan; Wolfgang Steglich

Publisher

John Wiley and Sons; Wiley (John Wiley & Sons); John Wiley & Sons Ltd.; Wiley (ISSN 1434-193X)

Published

2007

Language

EN

Field

Chemistry (Physical Sciences)