Total synthesis of 1-deoxy-7,8a-di-epi-castanospermine and formal synthesis of pumiliotoxin-251D

SULTANE, PRAKASH R.; MOHITE, AMAR R.; BHAT, RAMAKRISHNA G.

DR Home
→
PUBLICATIONS & PATENTS
→
JOURNAL ARTICLES
→
View Item

dc.contributor.author	SULTANE, PRAKASH R.	en_US
dc.contributor.author	MOHITE, AMAR R.	en_US
dc.contributor.author	BHAT, RAMAKRISHNA G.	en_US
dc.date.accessioned	2019-07-23T11:08:15Z
dc.date.available	2019-07-23T11:08:15Z
dc.date.issued	2012-10	en_US
dc.identifier.citation	Tetrahedron Letters, 53(44), 5856-5858.	en_US
dc.identifier.issn	0040-4039	en_US
dc.identifier.uri	http://dr.iiserpune.ac.in:8080/xmlui/handle/123456789/3600
dc.identifier.uri	https://doi.org/10.1016/j.tetlet.2012.08.061	en_US
dc.description.abstract	A concise and efficient synthesis of (6R,7S,8R,8aS)-6,7,8-trihydroxyindolizidine (1-deoxy-7,8a-di-epi-castanospermine) 2 is described. The synthesis employs cross metathesis in building the key intermediate 9 and is used effectively in constructing indolizidine skeleton for the total synthesis of 1-deoxy-7,8a-di-epi-castanospermine and also for the bicyclic framework of pumiliotoxin 251D 12, 13. The indolizidine skeleton is achieved in one pot sequence of transformations such as deprotection of Cbz group, reduction of double bond, and cyclization. The configurational and conformational structures of compound 10 are unambiguously confirmed by X-ray analysis.	en_US
dc.language.iso	en	en_US
dc.publisher	Elsevier B.V.	en_US
dc.subject	Dihydroxylation	en_US
dc.subject	Cross-metathesis	en_US
dc.subject	Wittig reaction	en_US
dc.subject	Cyclization	en_US
dc.subject	Castanospermine	en_US
dc.subject	Pumiliotoxin	en_US
dc.subject	2012	en_US
dc.title	Total synthesis of 1-deoxy-7,8a-di-epi-castanospermine and formal synthesis of pumiliotoxin-251D	en_US
dc.type	Article	en_US
dc.contributor.department	Dept. of Chemistry	en_US
dc.identifier.sourcetitle	Tetrahedron Letters	en_US
dc.publication.originofpublisher	Foreign	en_US