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A Formal Total Synthesis of Virantmycin: A Modular Approach towards Tetrahydroquinoline Natural Products
Author(s) -
Keck Daniel,
Vanderheiden Sylvia,
Bräse Stefan
Publication year - 2006
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.200600635
Subject(s) - chemistry , allylic rearrangement , total synthesis , intramolecular force , formal synthesis , combinatorial chemistry , natural product , organic chemistry , catalysis
A synthesis of an advanced intermediate towards the racemic form of the antiviral agent virantmycin has been developed featuring an intramolecular aza‐xylylene Diels–Alder reaction. The required arylthiocarbamate has been constructed using an efficient oxidative cyclization strategy. A novel synthetic approach to chlorine‐substituted allylic alcohols using an unprecedented palladium‐catalyzed cross‐coupling reaction of α,β‐unsaturated ketones and protected propargylic alcohols is reported.(© Wiley‐VCH Verlag GmbH & Co. KGaA, 69451 Weinheim, Germany, 2006)