Synthesis of Bioactive Natural Products by Asymmetric syn- and anti-Aldol Reactions

Abstract

The use of several variants of the asymmetric aldol reaction as key steps in the syntheses of bioactive target molecules is described.

Keywords: anti-aldol; asymmetric synthesis; chiral auxiliary; indanolamine; natural products; syn-aldol.

Figure 1

Some natural products synthesized by aldol reaction strategies

Figure 2

Structure of protease inhibitors 79 and 80

Scheme 1

Synthesis of hapalosin

Scheme 2

Synthesis of cryptophycin B

Scheme 3

Synthesis of tetrahydrolipstatin

Scheme 4

Synthesis of the pseudopeptide microbial agent AI-77-B

Scheme 5

Synthesis of sulfone fragment 43

Scheme 6

Completion of the synthesis of amphidinolide T1; DTBMP = 2,6-di-tert-butyl-4-methylpyridine

Scheme 7

Synthesis of protected 8-hydroxynonenoic acid 54

Scheme 8

Completion of (+)-jasplakinolide

Scheme 9

Synthesis of peloruside A intermediate 64

Scheme 10

Synthesis of intermediate 67 and completion of the synthesis of peloruside A

Scheme 11

Synthesis of 11-epi-stereocalpin A

Scheme 12

Synthesis of the compound with the proposed structure of stereocalpin A

Scheme 13

Synthesis of a bistetrahydrofuran ligand