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Studies Towards the Total Synthesis of Cycloaraneosene and Ophiobolin M: A General Strategy for the Construction of the 5−8 Bicyclic Ring System
Author(s) -
Ruprah Parminder K.,
Cros JeanPhilippe,
Pease J. Elizabeth,
Whittingham William G,
Williams Jonathan M. J.
Publication year - 2002
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 - 10.1002/1099-0690(200209)2002:18<3145::aid-ejoc3145>3.0.co;2-3
Subject(s) - bicyclic molecule , chemistry , ring (chemistry) , stereochemistry , total synthesis , combinatorial chemistry , organic chemistry
The synthesis of the core unit of cycloaraneosene and ophiobolin M has been investigated, following a general strategy applicable to both 5−8 bicyclic systems. The synthetic strategy includes a ring‐closing metathesis reaction to generate the central eight‐membered ring as well as a palladium‐mediated coupling of a Grignard reagent to introduce the exocyclic side‐chain. The stereochemistry of the ring junction is also discussed and moderate diastereoselectivity has been achieved. (© Wiley‐VCH Verlag GmbH, 69451 Weinheim, Germany, 2002)