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Synfacts 2005(0): 0008-0008
DOI: 10.1055/s-2005-865345
DOI: 10.1055/s-2005-865345
Synthesis of Natural Products and Drugs
© Georg Thieme Verlag Stuttgart · New York
Total Synthesis of (-)-SNF4435 C and
(+)-SNF4435 D
Contributor(s):
Philip Kocienski
K. A. Parker*, Y.-H. Lim
State University of New York at Stony Brook, USA
The Total Synthesis of (-)-SNF4435 C and (+)-SNF4435 D
J. Am. Chem. Soc. 2004, 126: 15968-15969
State University of New York at Stony Brook, USA
The Total Synthesis of (-)-SNF4435 C and (+)-SNF4435 D
J. Am. Chem. Soc. 2004, 126: 15968-15969
Further Information
Publication History
Publication Date:
20 July 2005 (online)
Key words
electrocyclization - biomimetic -
Significance
SNF4435 C and SNF4435 D are metabolites of Streptomyces spectabilis that display immunosuppressant and multidrug resistance reversal activity.
Comment
Parker and Lim adopt a biomimetic approach in which the tetraene (A) undergoes first a conrotatory π8a electrocyclization followed by a disrotatory π6s electrocyclization under the conditions of the Stille coupling (DMF, room temperature) to give a 4:1 mixture of the diastereoisomeric target molecules. The natural products are isolated as a 2.3:1 mixture (see also: J. E. Moses, R. M. Adlington, R. Rodriguez, S. J. Eade and J. E. Baldwin Chem. Commun. 2005, 1687-1689).