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Unified Syntheses of Cavicularin and Riccardin C: Addressing the Synthesis of an Arene Adopting a Boat Configuration
Author(s) -
Kostiuk Sarah L.,
Woodcock Timothy,
Dudin Leo F.,
Howes Peter D.,
Harrowven David C.
Publication year - 2011
Publication title -
chemistry – a european journal
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 1.687
H-Index - 242
eISSN - 1521-3765
pISSN - 0947-6539
DOI - 10.1002/chem.201101550
Subject(s) - regioselectivity , wittig reaction , halogenation , stereochemistry , combinatorial chemistry , sequence (biology) , convergent synthesis , chemistry , ring (chemistry) , total synthesis , organic chemistry , catalysis , biochemistry
Abstract Concise syntheses of the natural products cavicularin (ten steps) and riccardin C (seven steps) are reported. Key features of the new synthetic route are a convergent strategy to assemble acyclic precursors and a sequence of regioselective reduction and halogenation steps to facilitate Wittig macrocyclisation and transannular ring contraction reactions.