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A Carbohydrate‐Based Synthesis of the C13–C22 Fragment of Amphidinolide X
Author(s) -
Gurjar Mukund K.,
Yellol Gorakh S.,
Mohapatra Debendra K.
Publication year - 2012
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.201101605
Subject(s) - chemistry , tetrahydrofuran , wittig reaction , deoxygenation , stereochemistry , stereoselectivity , fragment (logic) , mitsunobu reaction , carbohydrate , total synthesis , combinatorial chemistry , organic chemistry , catalysis , algorithm , solvent , computer science
A facile carbohydrate‐based route was developed for the synthesis of the tetrahydrofuran (C13–C22) fragment of amphidinolide X. Starting from L ‐sorbose, the key reactions followed include the stereoselective synthesis of a quaternary center at C1, Barton–McCombie deoxygenation at C2, Mitsunobu inversion at C3, and chain elongation by a Wittig reaction at C5.