Convergent synthesis of the IJKLM-ring part of ciguatoxin CTX3C

Autor:	Hidethoshi Kawai, Daisuke Domon, Kenshu Fujiwara, Takanori Suzuki, Akio Murai
Rok vydání:	2005
Předmět:	chemistry.chemical_classification Ketone Stereochemistry Organic Chemistry Convergent synthesis Ether General Medicine Ring (chemistry) Biochemistry Aldehyde Adduct chemistry.chemical_compound chemistry Yield (chemistry) Drug Discovery Carbanion
Zdroj:	Tetrahedron Letters. 46:8285-8288
ISSN:	0040-4039
DOI:	10.1016/j.tetlet.2005.09.164
Popis:	Convergent synthesis of the IJKLM-ring part ( 2 ) of ciguatoxin CTX3C has been achieved from the I-ring and the L-ring parts ( 4 and 5 ) in total eight steps in 27% overall yield. The carbanion derived from 4 , stabilized by a dimethyldithioacetal S-oxide group, was readily reacted with aldehyde 5 to give an adduct, which was facilely transformed into the corresponding α,e-dihydroxy ketone 3 . The JK-ring formation from 3 under reductive conditions followed by oxidative M-ring cyclization efficiently led to the pentacyclic ether 2 . Improved synthesis of 6 , a synthetic intermediate for 4 , was also established.
Databáze:	OpenAIRE
Externí odkaz:	https://explore.openaire.eu/search/publication?articleId=doi_dedup___::140aaa4e3cb8d83b738f5aa955d7fe6b https://doi.org/10.1016/j.tetlet.2005.09.164 Zobrazit plný text záznamu Full Text from ScienceDirect