A formal total synthesis of (−)-kumausallene

Das, Shyamsundar ; Ramana, Chepuri V. (2015) A formal total synthesis of (−)-kumausallene Tetrahedron, 71 (45). pp. 8577-8584. 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.2015.09.027


Deacetylkumausyne—a penultimate intermediate in Tang's total synthesis of (−)-kumausallene has been synthesized employing a chiral pool approach and thus culminating in a formal total synthesis of kumausallene. The opening of an epoxide with alkyne (use of Birch reduction for the selective construction of E-pent-3-enyl group) and C-allylation have been used to introduce the pendant alkenyl side chains. Initial attempts to execute an alternative to Tang's route comprising a prior installation of the bromoallene unit via bromoetherification and subsequent SN2 displacement are unsuccessful. To overcome this, an alternative approach was developed to arrive at Deacetylkumausyne (another natural product that has been synthesized and characterized by Tang's group). Thus, this overall exercise has culminated in a formal total synthesis of (−)-kumausallene.

Item Type:Article
Source:Copyright of this article belongs to Elsevier Science.
Keywords:Bis-THF Natural Products; Deacetylkumausyne; Total Synthesis; Chiral Pool; Wittig Reaction
ID Code:105914
Deposited On:01 Feb 2018 16:50
Last Modified:01 Feb 2018 16:50

Repository Staff Only: item control page