A Chemoenzymatic Route to Chiral Intermediates Used in the Multikilogram Synthesis of a Gamma Secretase Inhibitor

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바이오화학분류

- 바이오정밀화학
  1. 용매
  2. 기타
- 화장품용 기능성소재
  1. 계면활성제⁄증점제
- 의료용 화학소재
  1. 치료제
  2. 식품첨가제

논문

A Chemoenzymatic Route to Chiral Intermediates Used in the Multikilogram Synthesis of a Gamma Secretase Inhibitor

학술지

Organic process research & development

저자명

Burns, Michael; Martinez, Carlos A.; Vanderplas, Brian; Wisdom, Richard; Yu, Shu; Singer, Robert A.

초록

A chemoenzymatic route for the production of an intermediate to a gamma secretase inhibitor is described. The route is robust and was run at multikilogram scale. The process employs both a transaminase catalyzed reductive amination of a substituted tetralone and an alcohol dehydrogenase catalyzed reduction of an α-ketoester to generate the two chiral centers in the molecule, with nearly perfect stereoselectivity. The process also features simple isolation schemes, including a direct drop isolation of the aminotetralin phosphate salt.Graphic Abstract <IMG SRC='http://pubs.acs.org/appl/literatum/publisher/achs/journals/content/oprdfk/2017/oprdfk.2017.21.issue-6/acs.oprd.7b00096/production/images/medium/op-2017-00096a_0006.gif'>

발행연도

2017

발행기관

American Chemical Society

ISSN

1083-6160

ISSN

1520-586x

권

호

페이지

pp.871-877