Total synthesis of squamotacin

Citation
Sc. Sinha et al., Total synthesis of squamotacin, J ORG CHEM, 64(19), 1999, pp. 7067-7073
Citations number
54
Categorie Soggetti
Chemistry & Analysis","Organic Chemistry/Polymer Science
Journal title
JOURNAL OF ORGANIC CHEMISTRY
ISSN journal
00223263 → ACNP
Volume
64
Issue
19
Year of publication
1999
Pages
7067 - 7073
Database
ISI
SICI code
0022-3263(19990917)64:19<7067:TSOS>2.0.ZU;2-0
Abstract
The first total synthesis of (+)-squamotacin, 1, which has shown cytotoxic selectivity for the human prostate tumor cell line, was; achieved in 27 ste ps and 0.83% yield starting with (+)-muricatacin, 4. All asymmetric centers in the bistetrahydrofuran fragment of the molecules were produced by the S harpless asymmetric dihydroxylation (AD) and the asymmetric epoxidation (AE ) reactions.