Structure elucidation and enantioselective total synthesis of the HMG-CoA reductase inhibitors FR901512 and FR901516

Masahiro Inoue; Masahisa Nakada

doi:10.1055/S-0029-1216980

Structure elucidation and enantioselective total synthesis of the HMG-CoA reductase inhibitors FR901512 and FR901516

Masahiro Inoue, Masahisa Nakada^*

^*Corresponding author for this work

School of Advanced Science and Engineering

Research output: Contribution to journal › Review article › peer-review

2 Citations (Scopus)

Abstract

The enantioselective total synthesis of the potent HMGCoA reductase inhibitors FR901512 (1) and FR901516 (2) is reviewed. FR901512 was prepared in 15 steps from commercially available compound via 2 in 16.3% overall yield (89% average yield). This study validated the applicability and reliability of the catalytic asymmetric Nozaki-Hiyama reactions that were developed by us. These reactions enabled the concise, efficient, and protecting-group-free enantioselective total syntheses of these new statins.

Original language	English
Pages (from-to)	3694-3707
Number of pages	14
Journal	Synthesis
Issue number	21
DOIs	https://doi.org/10.1055/S-0029-1216980
Publication status	Published - 2009 Dec 21

Keywords

Asymmetric catalysis
Enantioselective synthesis
Nozaki-Hiyama reaction
Structure elucidation
Total synthesis

ASJC Scopus subject areas

Catalysis
Organic Chemistry

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10.1055/S-0029-1216980

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title = "Structure elucidation and enantioselective total synthesis of the HMG-CoA reductase inhibitors FR901512 and FR901516",

abstract = "The enantioselective total synthesis of the potent HMGCoA reductase inhibitors FR901512 (1) and FR901516 (2) is reviewed. FR901512 was prepared in 15 steps from commercially available compound via 2 in 16.3% overall yield (89% average yield). This study validated the applicability and reliability of the catalytic asymmetric Nozaki-Hiyama reactions that were developed by us. These reactions enabled the concise, efficient, and protecting-group-free enantioselective total syntheses of these new statins.",

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author = "Masahiro Inoue and Masahisa Nakada",

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doi = "10.1055/S-0029-1216980",

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T1 - Structure elucidation and enantioselective total synthesis of the HMG-CoA reductase inhibitors FR901512 and FR901516

AU - Inoue, Masahiro

AU - Nakada, Masahisa

PY - 2009/12/21

Y1 - 2009/12/21

N2 - The enantioselective total synthesis of the potent HMGCoA reductase inhibitors FR901512 (1) and FR901516 (2) is reviewed. FR901512 was prepared in 15 steps from commercially available compound via 2 in 16.3% overall yield (89% average yield). This study validated the applicability and reliability of the catalytic asymmetric Nozaki-Hiyama reactions that were developed by us. These reactions enabled the concise, efficient, and protecting-group-free enantioselective total syntheses of these new statins.

AB - The enantioselective total synthesis of the potent HMGCoA reductase inhibitors FR901512 (1) and FR901516 (2) is reviewed. FR901512 was prepared in 15 steps from commercially available compound via 2 in 16.3% overall yield (89% average yield). This study validated the applicability and reliability of the catalytic asymmetric Nozaki-Hiyama reactions that were developed by us. These reactions enabled the concise, efficient, and protecting-group-free enantioselective total syntheses of these new statins.

KW - Asymmetric catalysis

KW - Enantioselective synthesis

KW - Nozaki-Hiyama reaction

KW - Structure elucidation

KW - Total synthesis

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DO - 10.1055/S-0029-1216980

M3 - Review article

AN - SCOPUS:72049101650

SN - 0039-7881

SP - 3694

EP - 3707

JO - Synthesis

JF - Synthesis

IS - 21

ER -

Structure elucidation and enantioselective total synthesis of the HMG-CoA reductase inhibitors FR901512 and FR901516

Abstract

Keywords

ASJC Scopus subject areas

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