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Total Synthesis and Structural Reassignment of the γ‐Lactone Polyketide from Diaporthe sp. SXZ‐19
Author(s) -
Yadav Jhillu S.,
Dutta Palash,
Ganganna Bogonda,
Srinivas Eedubilli
Publication year - 2015
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.201500811
Subject(s) - stereocenter , polyketide , chemistry , lactone , stereochemistry , natural product , total synthesis , metathesis , stereoselectivity , side chain , double bond , enantioselective synthesis , biosynthesis , organic chemistry , catalysis , polymer , polymerization , enzyme
The first stereoselective total synthesis of the proposed structure of the γ‐lactone from Diaporthe sp. SXZ‐19 was achieved by utilizing a convergent pathway. The four stereogenic centers were formed by employing Brown's asymmetric alkoxyallylboration reaction, and a cross‐metathesis reaction was used to construct the trans double bond of the γ‐lactone side chain. This synthesis led to a revision of proposed structural assignment of the natural product.