Pseudo-C3-Symmetric Tertiary Alcohol Building Block via Group-Selective Hydroalumination: A Synthesis of (−)-Malyngolide-Reference-Cited by-同舟云学术

Pseudo-C3-Symmetric Tertiary Alcohol Building Block via Group-Selective Hydroalumination: A Synthesis of (−)-Malyngolide

Published:2001-05-01 Issue:11 Volume:3 Page:1741-1744
ISSN:1523-7060
Container-title:Organic Letters
language:en
Short-container-title:Org. Lett.

Author:

Suzuki Takao¹,Ohmori Ken¹,Suzuki Keisuke¹

Affiliation:

1. Department of Chemistry, Tokyo Institute of Technology, and CREST, Japan Science and Technology Corporation (JST), O-okayama, Meguro-ku, Tokyo 152-8551, Japan

Publisher

American Chemical Society (ACS)

Subject

Organic Chemistry,Physical and Theoretical Chemistry,Biochemistry

Link

https://pubs.acs.org/doi/pdf/10.1021/ol015943v

Reference12 articles.

1. Structure and absolute configuration of malyngolide, an antibiotic from the marine blue-green alga Lyngbya majuscula Gomont

2. Group-Selective Hydroalumination: A Novel Route to Stereogenic tert-Alcohol Centers

3. The synthesis of Chiral Glycerides starting from D- and L-serine

4. Procedure for the hydroalumination of 8 withn-BuLi and DIBAL:To a solution of8(200 mg, 1.11 mmol) in THF (11 mL) was addedn-BuLi (1.50 M hexane solution, 0.74 mL, 1.1 mmol) at −78 °C. After stirring for 30 min, DIBAL (1.01 M hexane solution, 1.10 mL) was added. The temperature was gradually raised to 0 °C, and stirring was continued for 30 min. After quenching with saturated aqueous potassium sodium tartrate, extractive workup followed by flash column chromatography (SiO2, hexane/EtOAc = 85/15) gave4(160 mg, 79%, >99% ds) as a colorless oil.

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