- Abstract:
-
Mannich-type reaction of methyl phenylacetate with the N-tert-butylsulfinyl imine derived from (R)-tert-butylsulfinamide and (Z)-14-(pyridin-3'-yl)tetradec-11-enal has been used as the key step in the first asymmetric synthesis of (-)-nakinadine A. Both the 2,3-syn- and 2,3-anti-diastereoisomers were prepared; comparison of spectroscopic and specific rotation data facilitated assignment of the absolute (2S,3R,Z)-configuration within the natural product. (-)-(2S,3R,Z)-Nakinadine A was prepared...
Expand abstract - Publication status:
- Published
- Publisher copy:
- 10.1021/ol500096r
-
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- Journal:
- Organic letters
- Volume:
- 16
- Issue:
- 5
- Pages:
- 1354-1357
- Publication date:
- 2014-03-05
- DOI:
- EISSN:
-
1523-7052
- ISSN:
-
1523-7060
- URN:
-
uuid:bb7262bb-a230-4270-8990-1f30c3fbf645
- Source identifiers:
-
450903
- Local pid:
- pubs:450903
- Language:
- English
- Keywords:
- Copyright date:
- 2014
Journal article
(-)-(2S,3R,Z)-Nakinadine A: first asymmetric synthesis and absolute configuration assignment.
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