An Efficient Stereoselective Total Synthesis of Aculeatins A and B

Biswanath      Das; Martha      Krishnaiah; Siddavatam      Nagendra; Cheruku      R. Reddy

doi:10.2174/157017811795371494

Abstract

Aculeatins A and B, two naturally occurring bioactive spiroacetals, have been synthesized efficiently in stereoselective manner starting from 1-tetradecanal. The synthetic strategy involves Maruoka enantioselective allylation, diastereoselective iodine-induced electrophilic cyclization, alkylation of a chiral aldehyde and oxidative spirocyclization as the important steps.

Keywords: Aculeatins A and B, total synthesis, Maruoka allylation, iodine-induced cyclization, alkylation, spirocyclization, Zingiberaceae, tetradecanal, Trypazoma, ketone

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Letters in Organic Chemistry

Title: An Efficient Stereoselective Total Synthesis of Aculeatins A and B

Volume: 8 Issue: 4

Author(s): Biswanath Das, Martha Krishnaiah, Siddavatam Nagendra and Cheruku R. Reddy

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Keywords: Aculeatins A and B, total synthesis, Maruoka allylation, iodine-induced cyclization, alkylation, spirocyclization, Zingiberaceae, tetradecanal, Trypazoma, ketone

Abstract: Aculeatins A and B, two naturally occurring bioactive spiroacetals, have been synthesized efficiently in stereoselective manner starting from 1-tetradecanal. The synthetic strategy involves Maruoka enantioselective allylation, diastereoselective iodine-induced electrophilic cyclization, alkylation of a chiral aldehyde and oxidative spirocyclization as the important steps.

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Das Biswanath, Krishnaiah Martha, Nagendra Siddavatam and R. Reddy Cheruku, An Efficient Stereoselective Total Synthesis of Aculeatins A and B, Letters in Organic Chemistry 2011; 8 (4) . https://dx.doi.org/10.2174/157017811795371494