Retrosynthetic and Synthetic Chemistry on Amphotericin B. Synthesis of C(1)-C(20) and C(21)-C(38) Fragments and Construction of the 38-Membered Macrocycle

DOI: 10.1039/c39860000413

Source and publish data:

Journal of the Chemical Society. Chemical communications p. 413 - 416 (1986)

Update date:2022-08-04

Topics:

Authors:

Nicolaou, K. C.

Chakraborty, T. K.

Daines, R. A.

Simpkins, N. S.

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

Article abstract of DOI:10.1039/c39860000413

For the first time, amphotericin B (I) has been successfully derivatized and degraded to intermediates that have been converted into compounds (II) and (III) , projected as major key intermediates for a total synthesis; methods have been developed for the coupling of fragments (II) and (III) to give the ketophosphonate-aldehyde (28) and for the cyclization of this precursor to the 38-membered macrocyclic heptaenone (29) in 70-80percent yield.

Full text of DOI:10.1039/c39860000413

View Article Online / Journal Homepage / Table of Contents for this issue

View Article Online

Products guided by the article

Product name:(2S,3R,4S,5S)-2,4-Dimethyl-hexane-1,3,5-triol

Cas No:102614-37-9

R&D Labs maybe for 102614-37-9

Shandong Jusage Technology Co.,Ltd.

Contact:86-13406130167

Address:No.20,North Ride No.9 Road, Guangrao Economic Development Zone, Shandong Province
Shanghai Bosman Industrial Co., Ltd

Contact:86-21-63065878-8006

Address:Rm907, No.1611, North Sichuan Road, Hongkou District, Shanghai, 200080 China
WUHAN WELLSONG INT'L CO.,LTD

Contact:+86-27-85733560

Address:NO.308,QINGNIAN RD.,WUHAN,CHINA
Wuxi Highness Chemical Co.,Ltd

website:https://www.phtpharmatech.com/

Contact:86-510-81771080

Address:No58 East Xinguan Rd, Guanlin Town, Yixing City, Jiangsu China
Puyang Huicheng Electronic Material Co., Ltd

website:http://huichengchem.weba.testwebsite.cn/index_en.html

Contact:+86-393-8910800

Address:West Section Shengli Road, Puyang457000, China

Relevant to this article

MICELLAR CATALYSIS OF ORGANIC REACTIONS. PART 36. NUCLEOPHILIC AROMATIC SUBSTITUTION REACTIONS IN HYDROXY FUNCTIONALIZED MICELLES WITH BULKY HEAD GROUPS

Doi:10.1002/poc.610070809
(1994)
Zwitterionic-type molten salt: A mild and efficient organocatalyst for the synthesis of 3-aminoalkylated indoles via three-component coupling reaction

Doi:10.1055/s-0030-1259940
(2011)
Synthesis and anti-inflammatory activity of rac-2-(2,3-dihydro-1,4-benzodioxin)propionic acid and its R and S enantiomers

Doi:10.1016/S0223-5234(97)84016-0
(1997)
SYNTHESIS AND BIOLOGICAL ACTIVITY OF 1,3,4-SUBSTITUTED PYRAZOLIN-5-ONES

Doi:10.1007/BF00766685
(1985)
Doi:10.1016/S0040-4020(01)99418-9
(1966)
Concise, stereoselective route to the four diastereoisomers of 4-methylproline

Doi:10.1021/np070673w
(2008)

Article Doi