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Further Synthetic Studies Towards the Austrodorane Skeleton: Synthesis of Austrodoral
Author(s) -
Kulciţki Veaceslav,
Ungur Nicon,
Gavagnin Margherita,
Carbone Marianna,
Cimino Guido
Publication year - 2005
Publication title -
european journal of organic chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.825
H-Index - 155
eISSN - 1099-0690
pISSN - 1434-193X
DOI - 10.1002/ejoc.200400795
Subject(s) - chemistry , sesquiterpene , bicyclic molecule , stereochemistry , optically active , biomimetic synthesis , total synthesis , derivative (finance) , ring (chemistry) , contraction (grammar) , skeleton (computer programming) , organic synthesis , combinatorial chemistry , organic chemistry , catalysis , medicine , computer science , financial economics , economics , programming language
The synthesis of austrodoral ( 1 ), a marine nor ‐sesquiterpene that contains a unique bicyclic skeleton, has been achieved. The synthetic strategy is based on the ring contraction of a suitable optically active drimanic epoxy derivative, obtained from commercially available (+)‐sclareolide ( 4 ). Fluorosulfonic acid was found to promote the ring contraction efficiently. The nor ‐sesquiterpene hydrocarbon 13 , a key intermediate in the synthesis of sesquiterpene hydroquinones, has also been prepared in optically active form. (© Wiley‐VCH Verlag GmbH & Co. KGaA, 69451 Weinheim, Germany, 2005)