Synthesis of the C‐8–C‐24 Fragment of Maltepolide C by Using a Tandem Dihydroxylation/S N 2 Cyclization Sequence | Zendy

Mohapatra Debendra K. | Zendy; Reddy D. Sai | Zendy; Reddy G. Sudhakar | Zendy; Yadav Jhillu S. | Zendy

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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.

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