Asymmetric Total Synthesis of Lobophopyranone A and B

G. Sudhakar Reddy; Utkal Mani Choudhury; H. Sai Keerthana; K. Charan Naik; Debendra K. Mohapatra

doi:10.1055/a-2338-4462

Synthesis, Table of Contents

Synthesis 2025; 57(01): 99-108
DOI: 10.1055/a-2338-4462

paper

Special Topic Dedicated to Prof. H. Ila

Asymmetric Total Synthesis of Lobophopyranone A and B

G. Sudhakar Reddy

^aDepartment of Organic Synthesis and Process Chemistry, CSIR-Indian Institute of Chemical Technology, Hyderabad 500 007, India

^bAcademy of Scientific and Innovative Research (AcSIR), Ghaziabad 201 002, India

,

Utkal Mani Choudhury

^aDepartment of Organic Synthesis and Process Chemistry, CSIR-Indian Institute of Chemical Technology, Hyderabad 500 007, India

^bAcademy of Scientific and Innovative Research (AcSIR), Ghaziabad 201 002, India

,

H. Sai Keerthana

^aDepartment of Organic Synthesis and Process Chemistry, CSIR-Indian Institute of Chemical Technology, Hyderabad 500 007, India

,

K. Charan Naik

^aDepartment of Organic Synthesis and Process Chemistry, CSIR-Indian Institute of Chemical Technology, Hyderabad 500 007, India

^bAcademy of Scientific and Innovative Research (AcSIR), Ghaziabad 201 002, India

,

Debendra K. Mohapatra∗

^aDepartment of Organic Synthesis and Process Chemistry, CSIR-Indian Institute of Chemical Technology, Hyderabad 500 007, India

^bAcademy of Scientific and Innovative Research (AcSIR), Ghaziabad 201 002, India

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Abstract

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Dedicated to Prof. H. Ila on her 80^th Birthday celebrations, JNCASR, Bangalore, India

Abstract

The first asymmetric total synthesis and structural confirmation of lobophopyranone A and B have been accomplished from commercially available starting materials. Reagent-controlled Keck–Maruoka allylation, Grignard reaction, chelation-controlled Sakurai allylation, and acid-mediated one-step TBS ether deprotection followed by cyclization are the crucial stages in this synthesis that create the 2,6-disubstituted dihydropyranone component.

Key words

lobophopyranone - natural products - asymmetric synthesis - Keck–Maruoka allylations - Sakurai allylation - acid-mediated cyclization

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References

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