An enantioselective total synthesis of Sch-725674

Abstract

An enantioselective total synthesis of Sch-725674, a unique 14-membered macrolactone, has been accomplished in 13 steps. The step-wise dithiane alkylation served as a strategic step to assemble the upper and lower fragments of the molecule, whereas cross metathesis reaction, Yamaguchi macrolactonization and a substrate controlled stereoselective reduction are used as key steps to complete the total synthesis.

Enantioselective Modular Total Synthesis of Macrolides Sch725674 and C‐4‐epi‐Sch725674

“…egy. [5] A few more total syntheses of the same macrolactone were reported by Prasad et al [6] and Kaliappan et al [7] During the preparation of our manuscript, Reddy et al [8] reported the formal total synthesis of Sch725674 (1).…”

Sequential Enyne‐Metathesis/Diels–Alder Strategy: Rapid Access to Sugar–Oxasteroid–Quinone Hybrids

“…A new class of hybrid natural products, which are potentially biologically active, can be designed by combining structural units of two or more classes of natural products. As part of our research programme aimed at the synthesis of biologically active compounds, we previously reported our preliminary results on the design and synthesis of a new class of sugar–oxasteroid–quinone hybrids. This work was undertaken with the aim of combining the reactivity of the acetal moiety of furanose and the quinone unit with the steroidal backbone, as outlined in Scheme .…”

Total Synthesis of Antifungal Macrolide Sch 725674

“…Prasad and co-workers 3 have described the synthesis of 1 from tartaric acid using RCM as the key step. Kaliappan et al 4 have recently reported an enantioselective total synthesis of Sch 725674 utilizing dithiane alkylation as a strategic step. While our manuscript under preparation, three more syntheses of Sch 725674 were reported.…”