Synthesis and Biological Activity of Penaresidins A and B, Penazetidine A, and Related Analogues

Abstract

Since the first reports of their isolation, penaresidins A and B together with penazetidine A and related analogues have attracted interest from the synthetic community for their unique structural features, specifically the highly functionalized azetidine core. This review provides a comprehensive overview of the biological activity of the penaresidins, penazetidine, and their analogues together with reported synthetic strategies developed since their isolation.

1 Introduction

2 Biological Activity of Penaresidin A, Penaresidin B, and Penazetidine A and Related Analogues

3 Retrosynthetic Analysis

4 Penaresidin A Analogue (Kamikawa, 1995)

5 15-epi-Penaresidin A (Mori, 1995)

6 16-epi-Penazetidine A (Mori, 1996)

7 Penaresidin B (Yoda, 1997)

8 15-epi-Penaresidin B and Penaresidin B (Mori, 1997)

9 Penaresidin A and 16-nor-Penazetidine A (Knapp, 1997)

10 Substituted Penaresidin Core (Beauhaire and Ducrot, 1998)

11 Substituted Penaresidin Core (Ducrot, 1999)

12 Penaresidin A (Lin, 1999)

13 Penaresidin B (Yoda, 2003)

14 Penaresidin Structure-Reactivity Relationship (Kobayashi, 2007)

15 Penaresidin A (Raghavan, 2010)

16 Penaresidin A (Reddy, 2014)

17 Penaresidin B (Liu, 2015)

18 Penaresidin B (Yakura, 2018)

19 Penaresidin B (DuBois, 2020)

20 Penaresidin Analogues (Bodnár, 2021)

Key words

total synthesis - azetidine - penaresidin - sphingolipid - marine sponge

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