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Synthesis of the C‐8–C‐24 Fragment of Maltepolide C by Using a Tandem Dihydroxylation/S N 2 Cyclization Sequence
Author(s) -
Mohapatra Debendra K.,
Reddy D. Sai,
Reddy G. Sudhakar,
Yadav Jhillu S.
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.201500629
Subject(s) - chemistry , tandem , dihydroxylation , aldol reaction , fragment (logic) , stereoselectivity , stereochemistry , sharpless asymmetric dihydroxylation , hydroxylation , grignard reaction , sequence (biology) , enantioselective synthesis , organic chemistry , enzyme , catalysis , reagent , biochemistry , materials science , computer science , composite material , programming language
A highly stereoselective synthesis of the C‐8–C‐24 fragment of maltepolide C has been achieved in a convergent and efficient manner by utilizing a tandem Sharpless asymmetric dihydroxylation (SAD)/S N 2 cyclization reaction sequence as the key step. Other important steps include a Crimmins‐modified Evans aldol reaction, a Brown asymmetric allylation, a Horner–Wadsworth–Emmons olefination, and a Corey–Bakshi–Shibata (CBS) reduction.