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Protecting‐Group Directed Stereoselective Intramolecular Nozaki–Hiyama–Kishi Reaction: A Concise and Efficient Total Synthesis of Amphidinolactone A
Author(s) -
Mohapatra Debendra K.,
Das Pragna P.,
Pattanayak Manas R.,
Gayatri Gaddamanugu,
Sastry G. Narahari,
Yadav J. S.
Publication year - 2010
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.201000565
Subject(s) - chemistry , intramolecular force , total synthesis , stereoselectivity , stereochemistry , epoxide , convergent synthesis , lactone , ring (chemistry) , combinatorial chemistry , organic chemistry , catalysis
A convergent total synthesis of amphidinolactone A, a cytotoxic macrolide from the cultured dinoflagellate Amphidinium sp., is described in 13 linear steps. The key step in the synthetic sequence involves an intramolecular Nozaki–Hiyama–Kishi (NHK) reaction for the construction of the 13‐membered lactone ring by union of two fragments derived from a single chiral epoxide. The stereochemical outcome of the NHK reaction has been supported by computational studies.