Metal-mediated alkynediol cycloisomerization: First and second generation formal total syntheses of didemniserinolipid B

Das, Shyamsundar ; Induvadana, Boddeti ; Ramana, C. V. (2013) Metal-mediated alkynediol cycloisomerization: First and second generation formal total syntheses of didemniserinolipid B Tetrahedron, 69 (7). pp. 1881-1896. ISSN 0040-4020

Full text not available from this repository.

Official URL: http://www.sciencedirect.com/science/article/pii/S...

Related URL: http://dx.doi.org/10.1016/j.tet.2012.12.045

Abstract

A formal total synthesis of didemniserinolipid B was developed by employing a regioselective metal-mediated 6-endo-dig alkynol-cycloisomerization reaction. Two routes for the synthesis of key Burke's intermediate have been developed. Our initial approach involved the introduction of a C17-alkynol followed by Pd-mediated cycloisomerization and then coupling with the serinol unit prior to the introduction of an α,β-unsaturated ester unit through selective oxidation of 1°-OH followed by a two-carbon Wittig homologation. Alternatively, the second generation strategy featuring the serinol coupling with the C17-alkynol followed by alkyne addition to the epoxide and subsequent Au-mediated cycloisomerization of an acetonide protected alkynediol unit has been executed. This approach has avoided several late stage protection–deprotection events.

Item Type:Article
Source:Copyright of this article belongs to Elsevier Science.
Keywords:Alkynol-Cycloisomerization; Bicyclic Ketal; Palladium Catalysis; Gold Catalysis; Zipper Reaction
ID Code:105999
Deposited On:01 Feb 2018 16:52
Last Modified:01 Feb 2018 16:52

Repository Staff Only: item control page