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

Hangzhou Eastbiopharm Co.,Ltd.

Contact:+86-571-88931780

Address:Hangzhou,China
Hebei Think-Do Environment Co., Ltd

website:http://www.thinkdo-environment.com

Contact:0311-86510809-

Address:No 6, Shilian Middle Street, Circular Chemical Industry Park
Oren Hydrocarbons (Qingdao) Co., Ltd.

Contact:+86-532-68607667-801

Address:Room 3 # 302, No.9 Qingyun Road, Qingdao, China
Shanxi Tongji Pharmaceuticals Co., Ltd.

Contact:+86-359-3024784

Address:Xikuang South Road, Ruicheng County , Shanxi
Weifang Yukai Chemical Co.,Ltd.

website:http://www.yukaichem.com/en.html

Contact:+86-536-8865336

Address:binhai economic development zone，262737 shangdong，china

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