Studies of the tandem mukaiyama aldol-lactonization (TMAL) reaction: A concise and highly diastereoselective route to β-lactones applied to the total synthesis of the potent pancreatic lipase inhibitor, (-)-Panclicin D

DOI: 10.1016/S0040-4020(97)01029-6

Source and publish data:

Tetrahedron p. 16471 - 16488 (1997)

Update date:2022-08-12

Topics:

Authors:

Yang, Hong Woon

Zhao, Cunxiang

Romo, Daniel

Read Full Text PDF DownLoad Join now for total 90,000,000 free articles

Article abstract of DOI:10.1016/S0040-4020(97)01029-6

A concise and highly diastereoselective route to β-lactones has been developed based on a tandem Mukaiyama aldol-lactonization employing thiopyridylsilylketene acetals and various aldehydes. (-) - Panclicin D, a potent pancreatic lipase inhibitor, was synthesized using this methodology. Recent optimization and extensions of this method are described which include variation of the silyl group and leaving group of the ketene acetal.

Full text of DOI:10.1016/S0040-4020(97)01029-6

Products guided by the article

Product name:Lauroyl chloride

Cas No:112-16-3

R&D Labs maybe for 112-16-3

Lishui Nanming Chemical Co., Ltd(expird)

Contact:+86-0578-2134101，2697830

Address:No.19 Tongji Road Shuige Industrial zone
Shanghai Kefu Chemical Co.,Ltd.

Contact:+86-21-34616196

Address:Room601-602, Xuhui Business Building, No.168, Yude Road, Shanghai
Shanghai Coupling Pharmaceutical R&D Co., Ltd.(expird)

Contact:+86 021 50106671

Address:403 Room No.4 Buiding, No. 526 Ruiqing Road, Shanghai Zhangjiang Hi-Tech Park
Arshine Pharmaceutical Co., Limited

website:http://www.cnarshine.com

Contact:0731-88503671

Address:Room 1109.Block C3, Lugu Enterprise Plaza,No.27 Wenxuan Road,Changsha National Hi-Tech Industrial Development Zone,Hunan ,P.R.China
Weifang Arylchem Chemical Co., LTD

Contact:86-536-5217866

Address:Development Zone, Shouguang, Shandong Province

Relevant to this article

Tailored Synthesis of Skeletally Diverse Stemona Alkaloids through Chemoselective Dyotropic Rearrangements of β-Lactones

Doi:10.1002/anie.202102614
(2021)
The flavoenzyme azobenzene reductase AzoR from Escherichia coli binds roseoflavin mononucleotide (RoFMN) with high affinity and is less active in its RoFMN form

Doi:10.1021/bi400348d
(2013)
New Glycosides of Eriodictyol from Dracocephalum palmatum

Doi:10.1007/s10600-018-2499-4
()
HYDROGENATION OF CYCLOHEXENE ON DIFFERENT TYPES OF CATALYSTS

Doi:10.1007/BF01150879
(1992)
Synthesis of rhenium(I) and technetium(I) carbonyl/dithioether ligand complexes bearing 3,17β-estradiol

Doi:10.1016/S0960-894X(97)00396-X
(1997)
Molecular cloning and heterologous expression of progesterone 5β-reductase from Digitalis lanata Ehrh.

Doi:10.1016/j.phytochem.2005.11.013
(2006)

Article Doi