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

Squalestatin Sl 1 has been converted into its 4,7-bis(2-methoxyethoxymethyl) ether 4,5-dimethyl ester 11 and thence to its 3-(tert-butoxycarbonyl)amino derivative 12 via a Schmidt degradation. Acid-catalysed hydrolysis of 12 brought about a molecular rearrangement of the 2,8-dioxa; to the novel 6,8-...

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Published inJournal of the Chemical Society, Perkin Transactions 1 no. 11; pp. 1341 - 1347
Main Authors PROCOPIOU, PA, BAILEY, EJ, CHAN, C, INGLIS, GGA, LESTER, MG, SRIKANTHA, ARP, SIDEBOTTOM, PJ, WATSON, NS
Format Journal Article
LanguageEnglish
Published CAMBRIDGE Royal Soc Chemistry 1995
Subjects
Chemistry
Chemistry, Organic
Physical Sciences
Science & Technology
ALCOHOLS
REAGENT
PHOMA
NMR
SQUALENE SYNTHASE
INHIBITORS
STRUCTURE ELUCIDATION
ZARAGOZIC ACIDS
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Summary:Squalestatin Sl 1 has been converted into its 4,7-bis(2-methoxyethoxymethyl) ether 4,5-dimethyl ester 11 and thence to its 3-(tert-butoxycarbonyl)amino derivative 12 via a Schmidt degradation. Acid-catalysed hydrolysis of 12 brought about a molecular rearrangement of the 2,8-dioxa; to the novel 6,8-dioxa-bicyclo[3,2.1]octane ring system 3. Oxidation of 3 followed by methanolysis gave the novel spiroketal 17. Treatment of 3 with trimethyl phosphonoacetate gave the acyclic derivative 18.
ISSN:0300-922X
1364-5463
DOI:10.1039/p19950001341