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Approaches to the synthesis of cytochalasans. Part 6 . Synthesis of the C(14)–C(23) subunit of cytochalasins A, B. F and desoxaphomin
Author(s) -
Ackermann Jean,
WaespeŠarčevic̀ Nada,
Tamm Christoph
Publication year - 1984
Publication title -
helvetica chimica acta
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.74
H-Index - 82
eISSN - 1522-2675
pISSN - 0018-019X
DOI - 10.1002/hlca.19840670132
Subject(s) - synthon , chemistry , yield (engineering) , grignard reaction , stereochemistry , bromide , epoxide , catalysis , organic chemistry , materials science , reagent , metallurgy
The synthesis of methyl (4 R , 8 R ,)‐10‐bromo‐8‐methyl‐4‐(1,3,6‐trioxaheptane)‐2‐deceneoate ( 5 ), a synthon for the construction of the macrocyclic moieties of the cytochalasins A ( 1), B. (2) F (3) and desoxaphomin ( 4 ) is described. ( S )‐Glutamic acid ( 6 ) was transformed to the C 5 ‐epoxide 10 and 3‐methylglutaric acid ( 11 ) to the C 5 ‐bromide 15 . Coupling of both 10 and 15 by a CuI‐catalyzed Grignard reaction gave the decanol 16 in very high yield. The latter was transformed by several steps to synthon 5 .