Further Synthetic Studies Towards the Austrodorane Skeleton: Synthesis of Austrodoral | Zendy

Kulciţki Veaceslav | Zendy; Ungur Nicon | Zendy; Gavagnin Margherita | Zendy; Carbone Marianna | Zendy; Cimino Guido | Zendy

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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)

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