THE SQUALESTATINS - CLEAVAGE OF THE BICYCLIC CORE VIA THE NOVEL 6,8-DIOXABICYCLO[3.2.1]OCTANE RING-SYSTEM

Authors
PROCOPIOU PA BAILEY EJ CHAN C INGLIS GGA LESTER MG SRIKANTHA ARP SIDEBOTTOM PJ WATSON NS
Citation
Pa. Procopiou et al., THE SQUALESTATINS - CLEAVAGE OF THE BICYCLIC CORE VIA THE NOVEL 6,8-DIOXABICYCLO[3.2.1]OCTANE RING-SYSTEM, Journal of the Chemical Society. Perkin transactions. I, (11), 1995, pp. 1341-1347
Citations number
25
Categorie Soggetti
Chemistry Inorganic & Nuclear
Journal title
Journal of the Chemical Society. Perkin transactions. I → ACNP
ISSN journal
0300922X
Issue
11
Year of publication
1995
Pages
1341 - 1347
Database
ISI
SICI code
0300-922X(1995):11<1341:TS-COT>2.0.ZU;2-M
Abstract
Squalestatin Sl 1 has been converted into its 4,7-bis(2-methoxyethoxym ethyl) ether 4,5-dimethyl ester 11 and thence to its 3-(tert-butoxycar bonyl)amino derivative 12 via a Schmidt degradation. Acid-catalysed hy drolysis of 12 brought about a molecular rearrangement of the 2,8-diox a; to the novel 6,8-dioxa-bicyclo[3,2.1]octane ring system 3. Oxidatio n of 3 followed by methanolysis gave the novel spiroketal 17. Treatmen t of 3 with trimethyl phosphonoacetate gave the acyclic derivative 18.