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

Tianjin Pharmacn Medical Technology Co.,Ltd.

Contact:86-22-60122566ext.866(English),23359620

Address:Green Industrial Base, 6 Haitaifazhan Sixth Rd., Huayuan Industrial Area, Tianjin, 300384, China
Wuhan Better Organic Technology Inc.

Contact:13307163183

Address:Wuhan Economic&Technology Development Zone, Hubei
Changsha Yonta Industry Co., Ltd.

Contact:+ 86-731-8535 2228

Address:Rm.1717, North Bldg., No.368, East 2nd Ring Road(2nd Section)
Suzhou Sinosun Imp.&Exp. Corporation

website:http://www.szsinosun.com

Contact:+86-512-63488895,63488616

Address:No.758 East Jiangling Road Wujiang Economic & Technological Developmenty Zone Jiangsu China
wansheng

Contact:86-0311-88310000

Address:Room 1109 Sunshine Plaza,No.46 Tang Gudun Road,Jianghan District Wuhan Hubei

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