SYNTHETIC APPROACHES TO RAPAMYCIN - SYNTHESIS OF A C10-C26 FRAGMENT VIA A ONE-POT JULIA OLEFINATION REACTION

Authors
BELLINGHAM R JAROWICKI K KOCIENSKI P MARTIN V
Citation
R. Bellingham et al., SYNTHETIC APPROACHES TO RAPAMYCIN - SYNTHESIS OF A C10-C26 FRAGMENT VIA A ONE-POT JULIA OLEFINATION REACTION, Synthesis, (2), 1996, pp. 285
Citations number
47
Categorie Soggetti
Chemistry Inorganic & Nuclear
Journal title
Synthesis → ACNP
ISSN journal
00397881
Issue
2
Year of publication
1996
Database
ISI
SICI code
0039-7881(1996):2<285:SATR-S>2.0.ZU;2-C
Abstract
Keys steps in a synthesis of the C10-C26 fragment of the immunosuppres sant Rapamycin include (a) the use of a metallated benzothiazolyl sulf one in a one-pot Julia olefination to create the C21-C22 alkene stereo selectively and (b) a diastereoselective acid-catalysed cyclisation of a hydroxyl function onto a ketenedithioacetal (1,4-asymmetric inducti on) in order to create the oxane ring and fix the stereochemistry at C 11.