Synthesis of 1-aza-cryptophycin 1, an unstable cryptophycin. An unusual skeletal rearrangement

Authors
Barrow, RA Moore, RE Li, LH Tius, MA
Citation
Ra. Barrow et al., Synthesis of 1-aza-cryptophycin 1, an unstable cryptophycin. An unusual skeletal rearrangement, TETRAHEDRON, 56(21), 2000, pp. 3339-3351
Citations number
32
Categorie Soggetti
Chemistry & Analysis","Organic Chemistry/Polymer Science
Journal title
TETRAHEDRON
ISSN journal
00404020 → ACNP
Volume
56
Issue
21
Year of publication
2000
Pages
3339 - 3351
Database
ISI
SICI code
0040-4020(20000519)56:21<3339:SO11AU>2.0.ZU;2-W
Abstract
A total synthesis of cryptophycin 337 (1-aza-cryptophycin 1, 2), an analogu e of the potent antitumor antibiotic cryptophycin 1 (1), is described. Cryp tophycin 337 was unstable and underwent an unexpected skeletal rearrangemen t. (R)-Mandelic acid was used as the sole source of asymmetry for the synth esis of unit A. (C) 2000 Elsevier Science Ltd. All rights reserved.