Phorboxazole synthetic studies. 1. Construction of a C(3-19) subtarget exploiting an extension of the Petasis-Ferrier rearrangement.
Org Lett
; 1(6): 909-12, 1999 Sep 23.
Article
in En
| MEDLINE
| ID: mdl-10823221
ABSTRACT
[formula see text] In this, the first of two letters, we outline our overall strategy for the total synthesis of phorboxazoles A (1) and B (2), rare oxazole-containing macrolides possessing extraordinary antimitotic activity, and describe the assembly of a C(3-19) subtarget (-)-5 for the total synthesis of phorboxazole A. The synthesis of (-)-5 was achieved in 15 linear steps (12% overall yield), exploiting a modification of the Petasis-Ferrier rearrangement to construct the C(11-15) cis-tetrahydropyran. Dimethylaluminum chloride (Me2AlCl) proved to be the Lewis acid of choice for the Petasis-Ferrier rearrangement.
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Collection:
01-internacional
Database:
MEDLINE
Main subject:
Oxazoles
/
Heterocyclic Compounds, 4 or More Rings
Language:
En
Journal:
Org Lett
Journal subject:
BIOQUIMICA
Year:
1999
Document type:
Article
Affiliation country:
Estados Unidos