Synthesis and Biological Properties of the Cytotoxic 14‐Membered Macrolides Aspergillide A and B

Abstract

Scheme 1. Correct stereostructures of aspergillides A (1), B (2) and C (3).

Stereodivergent Total Synthesis of (+)‐Aspergillide B and (+)‐7‐epi‐Aspergillide A

“…3 These molecules showed modest cytotoxicity against mouse lymphatic leukemia cells. Further investigations showed these compounds to exhibit cytotoxicity toward a number of cancer cell lines including, HL‐60 (human promyelocytic leukemia), MDA‐MB‐231 (human breast carcinoma), and HT1080 (human fibrosarcoma) cell lines 4f. The striking structural complexity together with the biological activity of these macrolides has attracted several synthetic groups to target their total synthesis,4–7 which would allow the confirmation/revision of the absolute stereostructure of the molecules and also make them available to further investigations of their biological properties.…”

Applications of Mitsunobu Reaction in total synthesis of natural products

“…This macrolactone possess in vivo modest cytotoxic properties against lymphocytic leukemia cells in a mouse model. It also show cytotoxicity towards cancer cell lines including MDA‐MB‐231, HL‐60, and HT1080 cell lines . In 2012, Sridhar and Srihari achieved and reported a facile strategy for the stereoselective total synthesis of (+)‐7‐epi‐aspergillide A ( 238 ) (Scheme ) .…”

Studies towards the Total Synthesis of Aspergillide‐B

“…These natural products are characterized by a 14‐membered macrolactone core structure entrenched with a 2,6‐ cis or trans tetrahydropyran ring, 4‐hydroxy and 13‐methyl moiety. These molecules exhibit cytotoxicity to a number of different cancer cell lines including MDA‐MB‐231 (human breast carcinoma), HL‐60 (human promyelocytic leukemia) and HT1080 (human fibrosarcoma) cell lines . These properties, along with the challenging structural features encouraged a number of groups to pursue the synthesis of aspergillides A,B, C ,.…”