Journal
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION
Volume 56, Issue 4, Pages 1087-1091Publisher
WILEY-V C H VERLAG GMBH
DOI: 10.1002/anie.201609941
Keywords
alkaloids; diastereoselectivity; radical cyclization; spiro compounds; total synthesis
Categories
Funding
- Cabinet Office, Government of Japan through Funding Program for Next-Generation World-Leading Researchers [LS008]
- JSPS KAKENHI [JP16H01127, JP16H00999, 26253001]
- Grants-in-Aid for Scientific Research [25102007, 16H01147, 25102001, 16H00999, 16H05073, 26253001, 16H01127] Funding Source: KAKEN
Ask authors/readers for more resources
Stereoselective total syntheses of (-)-histrionicotoxin and (-)-histrionicotoxin 235A are described. The 1-azaspiro[5.5]undecane skeleton was constructed diastereoselectively by a radical translocation-cyclization reaction involving a chiral cyclic acetal; the use of tris( trimethylsilyl) silane was crucial for the high diastereoselectivity. The cyclization product was converted into (-)-histrionicotoxin 235A through a one-pot partial-reduction-allylation reaction of a derivative containing an unprotected lactam. Finally, two terminal alkenes were transformed into enynes with the 1,3-amino alcohol protected as an oxathiazolidine oxide to complete the total synthesis of (-)-histrionicotoxin.
Authors
I am an author on this paper
Click your name to claim this paper and add it to your profile.
Reviews
Recommended
No Data Available