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Review
. 2016 Jul 21;21(7):951.
doi: 10.3390/molecules21070951.

Recent Advances in Substrate-Controlled Asymmetric Induction Derived from Chiral Pool α-Amino Acids for Natural Product Synthesis

Seung-Mann Paek  1 , Myeonggyo Jeong  2 , Jeyun Jo  3 , Yu Mi Heo  4 , Young Taek Han  5 , Hwayoung Yun  6
Affiliations
Review

Recent Advances in Substrate-Controlled Asymmetric Induction Derived from Chiral Pool α-Amino Acids for Natural Product Synthesis

Seung-Mann Paek et al. Molecules. .

Abstract

Chiral pool α-amino acids have been used as powerful tools for the total synthesis of structurally diverse natural products. Some common naturally occurring α-amino acids are readily available in both enantiomerically pure forms. The applications of the chiral pool in asymmetric synthesis can be categorized prudently as chiral sources, devices, and inducers. This review specifically examines recent advances in substrate-controlled asymmetric reactions induced by the chirality of α-amino acid templates in natural product synthesis research and related areas.

Keywords: asymmetric induction; chiral pool; natural product; total synthesis; α-amino acid.

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Conflict of interest statement

The authors declare no conflict of interest.

Figures

Figure 1
Figure 1
Three categories of chiral pool use in asymmetric synthesis.
Figure 2
Figure 2
Representative α-amino acids.
Scheme 1
Scheme 1
Total syntheses of castanospermines 4 and 7.
Scheme 2
Scheme 2
Total synthesis of (−)-allonorsecurinine (10).
Scheme 3
Scheme 3
Total syntheses of ent-citrinalin B (15) and cyclopiamine B (16).
Scheme 4
Scheme 4
Total synthesis of penibruguieramine A (22).
Scheme 5
Scheme 5
Cu-catalyzed arylation of cyclo-(Trp-Phe) 23.
Scheme 6
Scheme 6
Total synthesis of (+)-naseseazines A and B.
Scheme 7
Scheme 7
Diastereoselective cyclization for pyrroloindoline skeleton.
Scheme 8
Scheme 8
Total syntheses of (−)-brevicompanine B (38) and (+)-aszonalenin (40).
Scheme 9
Scheme 9
Total syntheses of verruculogen (45) and fumitremorgin A (46).
Scheme 10
Scheme 10
Total synthesis of (−)-acetylaranotin (49).
Scheme 11
Scheme 11
Total synthesis of rigidiusculamide A (53).
Scheme 12
Scheme 12
Total synthesis of (−)-α-kainic acid (60).
Scheme 13
Scheme 13
Total synthesis of iso-haouamine B (64).
Scheme 14
Scheme 14
Total synthesis of (+)-erysotramidine (70).
Scheme 15
Scheme 15
Total syntheses of (+)-241D (74) and isosolenopsin (76).
Scheme 16
Scheme 16
De novo synthesis of orthogonally protected legionaminic acid 80.
See this image and copyright information in PMC

References

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