A carbohydrate approach for the formal total synthesis of (-)-aspergillide C

Pabbaraja Srihari; Namballa Hari Krishna; Ydhyam Sridhar; Ahmed Kamal

doi:10.3762/bjoc.10.329

A carbohydrate approach for the formal total synthesis of (-)-aspergillide C

Beilstein J Org Chem. 2014 Dec 23:10:3122-6. doi: 10.3762/bjoc.10.329. eCollection 2014.

Authors

Pabbaraja Srihari¹, Namballa Hari Krishna², Ydhyam Sridhar¹, Ahmed Kamal³

Affiliations

¹ Division of Natural Products Chemistry, CSIR-Indian Institute of Chemical Technology, Hyderabad, 500007, India.
² Division of Natural Products Chemistry, CSIR-Indian Institute of Chemical Technology, Hyderabad, 500007, India ; Department of Medicinal Chemistry, National Institute of Pharmaceutical Education and Research, Hyderabad, 500037, India ; Medicinal Chemistry & Pharmacology, CSIR-Indian Institute of Chemical Technology, Hyderabad, 500007, India.
³ Department of Medicinal Chemistry, National Institute of Pharmaceutical Education and Research, Hyderabad, 500037, India ; Medicinal Chemistry & Pharmacology, CSIR-Indian Institute of Chemical Technology, Hyderabad, 500007, India.

Abstract

An enantioselective formal total synthesis of aspergillide C is accomplished using commercially available tri-O-acetyl-D-galactal employing a Ferrier-type C-glycosylation, utilizing a Trost hydrosilylation and protodesilylation as key reactions.

Keywords: Ferrier-type C-glycosylation; alkynylation; chiron approach; macrolide.