Neopeltolide, a new promising antitumoral agent

Abstract

Neopeltolide seems to be a new promising antitumoral agent. The isolation, biological activity, as well as the chemical syntheses of neopeltolide are reported.

Total Synthesis and Biological Evaluation of (+)‐Neopeltolide and Its Analogues

“…These biological and structural aspects of neopeltolide spurred the interest of synthetic organic chemists. As a consequence, seven total syntheses, including ours, and two formal syntheses have been recorded to date 5–12. In addition, Kozmin and co‐workers have recently reported that synthetic neopeltolide targets cytochrome bc 1 complex and may inhibit mitochondrial Adenosine triphosphate synthesis 8…”

“…As a consequence, seven total syntheses, including ours, and two formal syntheses have been recorded to date. [5][6][7][8][9][10][11][12] In addition, Kozmin and co-workers have recently reported that synthetic neopeltolide targets cytochrome bc 1 complex and may inhibit mitochondrial Adenosine triphosphate synthesis. [8] Herein, we describe in detail the total synthesis of the originally proposed (1) and correct (2) structures of neopeltolide by exploiting our newly developed Suzuki-Miyaura coupling/ring-closing metathesis strategy for the synthesis of multi-substituted tetrahydropyrans.…”

Stereoselective Synthesis of 2,6‐cis‐Tetrahydropyrans through a Tandem Allylic Oxidation/Oxa‐Michael Reaction Promoted by the gem‐Disubstituent Effect: Synthesis of (+)‐Neopeltolide Macrolactone

“…Encouraged by the efficiency and versatility of the tandem allylic oxidation/oxa‐Michael reaction, we embarked on a stereoselective synthesis of (+)‐neopeltolide macrolactone ( 21 ). The marine macrolide (+)‐neopeltolide ( 19 ) is an extremely potent inhibitor of tumor‐cell proliferation15 and has attracted considerable interest from a number of synthetic research groups 16–18. We envisioned that the embedded 2,6‐ cis ‐4‐hydroxy‐THP could be constructed by using the tandem allylic oxidation/oxa‐Michael reaction as the key bond‐forming step (Scheme ).…”

Contemporary Strategies for the Synthesis of Tetrahydropyran Derivatives: Application to Total Synthesis of Neopeltolide, a Marine Macrolide Natural Product

“…In the past years, neopeltolide has served as an ideal target compound for synthetic chemists to showcase their creativity in how to construct the tetrahydropyran ring in an efficient and stereoselective manner. This review summarizes the total/formal syntheses of neopeltolide, highlighting the synthetic strategies exploited for constructing the tetrahydropyran ring [ 63 , 64 ].…”