Total synthesis, biological evaluation of dendrodolides A–D and their analogues. Issue 32 (11th August 2016)

• Record Type: Journal Article
• Authors: Poornima, B.; Venkanna, A.; Swetha, B.; Kamireddy, Karthik reddy; Siva, Bandi; Phani Babu, V.S.; Ummanni, Ramesh; Babu, K. Suresh
• Is Part Of: Tetrahedron. Volume 72:Issue 32(2016)
• Page Start: 4789
• Page End: 4797
• Publication Date: 2016-08-11
• Subjects: Macrolides -- Yamaguchi esterification -- RCM approach -- Jacobsen hydrolytic kinetic resolution -- Analogues -- Cytotoxic activity -- SAR studies; Chemistry, Organic -- Periodicals; 547.005
• DOI: 10.1016/j.tet.2016.06.042
• Languages: English
• ISSNs: 0040-4020

Abstract

Abstract: A concise total synthesis of dendrodolides A–D (1–4 ) has been accomplished in 10 steps from commercially available (R)-propylene oxide and 3-buten-1-ol as starting materials. The key steps involved in the synthesis are Jacobsen hydrolytic kinetic resolution, epoxide ring opening with 2-allyl-1, 3-dithiane, Yamaguchi esterification and ring-closing metathesis (RCM). In addition, a series of ester derivatives were prepared utilizing Yamaguchi esterification at the C-3 position of the dendrodolide core and screened for their efficacy against cancer cell lines. Graphical abstract: