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(Trimethylstannyl)methyllithium as a Source of a Methylene Bridge Connecting Two Acyl Groups: A Potential Route to D ‐Mycaroside
Author(s) -
Sato Tadashi,
Ariura Shigeki
Publication year - 1993
Publication title -
angewandte chemie international edition in english
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 5.831
H-Index - 550
eISSN - 1521-3773
pISSN - 0570-0833
DOI - 10.1002/anie.199301051
Subject(s) - methylene , epimer , yield (engineering) , methylene bridge , methyllithium , chemistry , bridge (graph theory) , block (permutation group theory) , stereochemistry , medicinal chemistry , mathematics , physics , combinatorics , medicine , thermodynamics
β‐Ketoaldehydes are conveniently accessible in acceptable yields, if esters are initially treated with two equivalents of the masked methylene dianion Me 3 SnCH 2 Li and then with methyl formate. In this way, for example, 1 can be obtained without epimerization in 66% yield, which might open a simpler access to D‐mycarose, an important antibiotic building block.