Synthetic studies of halichondrin B, an antitumor polyether macrolide isolated from a marine sponge. 6. Synthesis of the C1 - C15 unit via stereoselective construction of the B and A rings by kinetically and thermodynamically controlled Michael reactions with the aid of computational search for dominant conformers

DOI: 10.1248/cpb.45.1265

Source and publish data:

Chemical and Pharmaceutical Bulletin p. 1265 - 1281 (1997)

Update date:2022-08-03

Topics:

Authors:

Horita, Kiyoshi

Hachiya, Shun-Ichiro

Yamazaki, Tatsuya

Naitou, Tae

Uenishi, Jun'ichi

Yonemitsu, Osamu

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

Article abstract of DOI:10.1248/cpb.45.1265

The C1 - C15 unit of halichondrin B was synthesized starting from D- glucose via stereoselective construction of the B and A rings, which have 2,6-trans- and 2,6-cis-disubstituted tetrahydropyran rings, respectively. With the aid of MM2 calculations kinetically and thermodynamically controlled Michael reactions were successfully applied for the construction of the B and A rings, respectively.

Full text of DOI:10.1248/cpb.45.1265

NII-Electronic Library Service

Products guided by the article

Product name:6-O-benzoyl-3-O-benzyl-α/β-D-glucopyranose

Cas No:142657-25-8

R&D Labs maybe for 142657-25-8

Xuzhou Tianrun Chemical Co.,Ltd

website:http://www.tianrunchem.cn

Contact:86-516-83832636

Address:fuxing road
JIANGXI XINXIN CHEMICAL CO., LTD.

Contact:86-15957176628

Address:INDUSTRY ROAD 1, INDUSTRIAL PARK, HEKOU TOWN,YANSHAN COUNTY, JIANGXI PROVINCE, CHINA
Changsha Yonta Industry Co., Ltd.

Contact:+ 86-731-8535 2228

Address:Rm.1717, North Bldg., No.368, East 2nd Ring Road(2nd Section)
Amadis Chemical Co., Ltd.

website:http://www.amadischem.com

Contact:86-571-89925085

Address:Watts Cosine.No.166.Xiangmao Road.
Synasia Inc

Contact:17316303296

Address:240 Amboy Ave

Relevant to this article

New phosphine-imine ligands derived from D-gluco- and D-galactosamine in Pd-catalysed asymmetric allylic alkylation

Doi:10.1016/j.tetlet.2015.06.031
(2015)
Synthesis, characterization and preliminary anticonvulsant evaluation of some 4-alkyl-1,2,4-triazoles

Doi:10.1016/j.ejmech.2012.11.026
(2013)
One-pot synthesis of 2,3-dihydroquinazolin-4(1H)-ones by Fe₃O₄@SiO₂-imid-PMAⁿ nano-catalyst under ultrasonic irradiation and reflux conditions

Doi:10.1007/s00706-016-1832-5
(2017)
Coupling of low-order organocopper complexes with organoiron cations; Synthesis of tamandron, a novel potentially antiandrogenic analogue of tamoxifen

Doi:10.1039/c39920000635
(1992)
Synthesis of 4-(1,3-dioxo-2,3-dihydro-1H-2-indenyl) substituted 1-benzylpyrrole-3-carboxylates via a tandem four-component reaction

Doi:10.1016/j.crci.2012.10.003
(2013)
Highly practical synthesis of nitriles and heterocycles from alcohols under mild conditions by aerobic double dehydrogenative catalysis

Doi:10.1021/ol400459y
(2013)

Article Doi

DOI: 10.1248/cpb.45.1265