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Total Synthesis of Natural (+)‐Lasonolide A
Author(s) -
Kang Sung Ho,
Kang Suk Youn,
Kim Chul Min,
Choi Hyeongwook,
Jun HyukSang,
Lee Byeong Moon,
Park Chul Min,
Jeong Joon Won
Publication year - 2003
Publication title -
angewandte chemie international edition
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 5.831
H-Index - 550
eISSN - 1521-3773
pISSN - 1433-7851
DOI - 10.1002/anie.200352016
Subject(s) - total synthesis , stereochemistry , chemistry , enantioselective synthesis , sulfone , intramolecular force , tetrahydropyran , acetal , michael reaction , aldehyde , polyketide , wittig reaction , double bond , biosynthesis , ring (chemistry) , enzyme , organic chemistry , catalysis
The diastereoselective differentiation of two methylene groups of a cyclic acetal is a unique feature of a highly enantioselective total synthesis of natural (+)‐lasonolide A (see picture), which is used to create the C22 quaternary asymmetric center. Other key strategies are the use of a sulfone–sulfide as a three‐carbon fragment with two latent trans double bonds and macrocyclization through an intramolecular Horner–Emmons reaction.