Synthetic studies of halichondrin B, an antitumor polyether macrolide isolated from a marine sponge. 7. Synthesis of two C27-C36 units via construction of the F ring and completely stereoselective C-glycosylation using mixed Lewis acids

DOI: 10.1248/cpb.45.1558

Source and publish data:

Chemical and Pharmaceutical Bulletin p. 1558 - 1572 (1997)

Update date:2022-08-03

Topics:

Authors:

Horita, Kiyoshi

Sakurai, Youji

Nagasawa, Masaaki

Yonemitsu, Osamu

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

Article abstract of DOI:10.1248/cpb.45.1558

Two C27-C36 units of halichondrin B were synthesized starting from a C31-C34 alcohol, which was easily available from dimethyl L-tartrate, via construction of the F ring, methylation at the C31 position and C- glycosylation. These crucial reactions proceeded completely stereoselectively, and in particular the stereoselective C-glycosylation with allyltrimethylsilane took place only in the presence of both of two Lewis acids, boron trifluoride etherate and trimethylsilyl triflate.

Full text of DOI:10.1248/cpb.45.1558

NII-Electronic Library Service

Products guided by the article

Product name:(R)-((S)-2,2-Diethyl-[1,3]dioxolan-4-yl)-(4-methoxy-benzyloxy)-acetaldehyde

Cas No:174968-09-3

R&D Labs maybe for 174968-09-3

Nanjing Ruizhi Industry & Technologh Co.，Ltd.

Contact:+86-25-86808110

Address:441-4-A5,NO.12 Longzang Avenue,Yuhuatai District,210039,Nanjing
Xuzhou Tianrun Chemical Co.,Ltd

website:http://www.tianrunchem.cn

Contact:86-516-83832636

Address:fuxing road
Jiangsu Cale New Material Co.ltd

Contact:+86-515-88334667/88203550

Address:Zhongshan 3rd Road, Coastal Chemical Industry Park, Yancheng, Jiangsu, China
XZL BIO-TECHNOLOGY CO., LTD.

Contact:0086 533 2282832

Address:Zibo，Shandong
Suzhou Wedo Chemicals Co., Ltd.

Contact:86 512 58100425

Address:Zonger Road, DongSha Industry Park , Zhangjiagang, Jiangsu, China

Relevant to this article

Design and synthesis of new hypocholesterolemic organosilanes with antioxidant properties

Doi:10.1016/0960-894X(96)00063-7
(1996)
Defluorination of 4-fluorothreonine by threonine deaminase

Doi:10.1039/d0ob01358g
(2020)
Improved synthesis of 1-oxo-1,2,3,4-tetrahydroacridine-9-carboxylic acids from isatins and 1,3-cyclohexanedione

Doi:10.3987/COM-12-12479
(2012)
Synthetic studies on sialoglycoconjugates 82: First total synthesis of sialyl globopentaosyl ceramide (V³Neu5AcGb₅Cer) and its positional isomer (V⁶Neu5AcGb₅Cer) 1,2

Doi:10.1080/07328309608005436
(1996)
Ligand substitution reactions on aquapentachloro- and hexachloroplatinic acid - Synthesis and characterization of tetrachloroplatinum(IV) complexes with heterocyclic N,N donors

Doi:10.1002/zaac.200390119
(2003)
Sulfonium ylides. 6. New reaction of intramolecular cyclization of phthalimido-containing keto-stabilized sulfonium ylides

Doi:10.1007/BF01433752
(1996)

Article Doi