e.g. Filippa Pettersson or Cancer Res. 75(6) , 1102-12, (2015) or 10.1002/anie.201600521

Enantioselective construction of heterocycles. Synthesis of (R, R)-solenopsin B

DF Taber, PB Deker, HM Fales, TH Jones…

Index: Taber, Douglass F.; Deker, P. Bruce Journal of Organic Chemistry, 1988 , vol. 53, # 13 p. 2968 - 2971

Full Text: HTML

Citation Number: 46

Abstract

An enantioselective route to solenopsin B (l), the major saturated component of the alkaloid mixture isolated from the venom of the fire ant, Solenopsis invicta, is reported. The key transformation in this synthesis is the smooth thermolytic cyclization of alkenyl azide 3. The precursor to 3, alcohol 4, is prepared by stereoselective reduction of an enantiomerically pure P-keto ester.

4,7,7-trimethyl-3-exo-(1-naphthyl)bicyclo[2.2.1]hept-2-exo-yl 3-oxohexadecanoate Structure

4,7,7-trimethyl...

~%

(S)-3-hydroxyhexadecyl 4-methylbenzenesulfonate Structure

(S)-3-hydroxyhe...

(S)-(1S,2R,3R,4S)-4,7,7-trimethyl-3-(naphthalen-1-yl)bicyclo[2.2.1]heptan-2-yl 3-hydroxyhexadecanoate Structure

(S)-(1S,2R,3R,4...

~%

(S)-3-hydroxyhexadecyl 4-methylbenzenesulfonate Structure

(S)-3-hydroxyhe...

(+)-(S)-hexadecane-1,3-diol Structure

(+)-(S)-hexadec...

~%

(-)-(S)-nonadec-1-en-6-ol Structure

(-)-(S)-nonadec...

4,7,7-trimethyl-3-exo-(1-naphthyl)bicyclo[2.2.1]hept-2-exo-yl 3-oxohexadecanoate Structure

4,7,7-trimethyl...

~%

(-)-(S)-nonadec-1-en-6-ol Structure

(-)-(S)-nonadec...

(S)-(1S,2R,3R,4S)-4,7,7-trimethyl-3-(naphthalen-1-yl)bicyclo[2.2.1]heptan-2-yl 3-hydroxyhexadecanoate Structure

(S)-(1S,2R,3R,4...

~%

(-)-(S)-nonadec-1-en-6-ol Structure

(-)-(S)-nonadec...

(-)-(S)-nonadec-1-en-6-ol Structure

(-)-(S)-nonadec...

~86%

(R)-nonadec-1-en-6-yl azide Structure

(R)-nonadec-1-e...

(+)-(S)-hexadecane-1,3-diol Structure

(+)-(S)-hexadec...

~%

(R)-nonadec-1-en-6-yl azide Structure

(R)-nonadec-1-e...

(S)-3-hydroxyhexadecyl 4-methylbenzenesulfonate Structure

(S)-3-hydroxyhe...

~%

(R)-nonadec-1-en-6-yl azide Structure

(R)-nonadec-1-e...

4,7,7-trimethyl-3-exo-(1-naphthyl)bicyclo[2.2.1]hept-2-exo-yl 3-oxohexadecanoate Structure

4,7,7-trimethyl...

~%

(R)-nonadec-1-en-6-yl azide Structure

(R)-nonadec-1-e...

(S)-(1S,2R,3R,4S)-4,7,7-trimethyl-3-(naphthalen-1-yl)bicyclo[2.2.1]heptan-2-yl 3-hydroxyhexadecanoate Structure

(S)-(1S,2R,3R,4...

~%

(R)-nonadec-1-en-6-yl azide Structure

(R)-nonadec-1-e...

(S)-(1S,2R,3R,4S)-4,7,7-trimethyl-3-(naphthalen-1-yl)bicyclo[2.2.1]heptan-2-yl 3-hydroxyhexadecanoate Structure

(S)-(1S,2R,3R,4...

~91%

(+)-(S)-hexadecane-1,3-diol Structure

(+)-(S)-hexadec...

4,7,7-trimethyl-3-exo-(1-naphthyl)bicyclo[2.2.1]hept-2-exo-yl 3-oxohexadecanoate Structure

4,7,7-trimethyl...

~%

(+)-(S)-hexadecane-1,3-diol Structure

(+)-(S)-hexadec...

4,7,7-trimethyl-3-exo-(1-naphthyl)bicyclo[2.2.1]hept-2-exo-yl 3-oxohexadecanoate Structure

4,7,7-trimethyl...

~78%

(S)-(1S,2R,3R,4S)-4,7,7-trimethyl-3-(naphthalen-1-yl)bicyclo[2.2.1]heptan-2-yl 3-hydroxyhexadecanoate Structure

(S)-(1S,2R,3R,4...