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Approaches to the Synthesis of Cytochalasans Part9 . A versatile concept leading to all structural types of cytochalasans
Author(s) -
Ackermann Jean,
Matthes Michael,
Tamm Christoph
Publication year - 1990
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.19900730113
Subject(s) - chemistry , derivative (finance) , bicyclic molecule , combinatorial chemistry , stereochemistry , economics , financial economics
Abstract Starting from D‐glutamic acid ( 5 ), the bicyclic compounds 4a and 4b were synthesized via 17 ( Schemes 1 and 2 ). The reaction leading to 4g and 4h with LiCuPh 2 was not successful. But treatment of the N‐protected model lactams 19 , 21 , and 22 with Li 2 Cu(CN)Ph 2 gave the amino ketones 24 , 26 , and 27 , respectively ( Scheme 3 ). The desired compound 23 was obtained from 20. Conversion of the unprotected lactams 28 , 31 , and 32 gave the phenyl derivative 34 in excellent yields. Ester 35 was transformed to the α ‐amino‐γ‐ oxo‐acid derivative 36. This conversion opens a novel access to this type of compounds.