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A Partial Synthesis of the Skeleton of Deoxypumiloside, a Putative Intermediate in Camptothecin Biosynthesis
Author(s) -
Thomas Olivier P.,
Zaparucha Anne,
Husson HenriPhilippe
Publication year - 2002
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 - 10.1002/1099-0690(20021)2002:1<157::aid-ejoc157>3.0.co;2-s
Subject(s) - chemistry , camptothecin , biosynthesis , indole test , stereochemistry , amine gas treating , allylic rearrangement , chemical synthesis , lactam , biomimetic synthesis , biochemistry , organic chemistry , in vitro , enzyme , catalysis
Ajmalicine ( 3 ) was used as the starting material for the synthesis of a camptothecin‐like skeleton. After C‐21 activation through allylic conjugation, regiospecific tertiary amine oxidation was achieved with mercury salts. Subsequent biomimetic oxidation of the indole nucleus then gave quinolone lactam 14 . A two‐step process finally afforded 4 , a close analogue of deoxypumiloside ( 5 ), one of the putative intermediates in the biosynthesis of camptothecin.