What question did this study set out to answer?

The aim is to achieve the first total enantioselective synthesis of (-)-citrifelin A.

February 5, 2026

Enantioselective Total Synthesis of Citrifelin A via the Oxa-Pictet–Spengler Reaction and Acid-Promoted Dihydropyran Formation

Key Points

The aim is to achieve the first total enantioselective synthesis of (-)-citrifelin A.
Utilized the oxa-Pictet-Spengler reaction to construct the core structure.
Employed acid-promoted dihydropyran formation for stereocontrol.
Conducted an eight-step synthesis path for total synthesis.
Started from known chemical materials.
Achieved synthesis of (-)-citrifelin A with an overall yield of 17%.
Successfully constructed the tetracyclic framework through specified reactions.

Abstract

The enantioselective first total synthesis of (-)-citrifelin A is described herein. We found that the oxa-Pictet-Spengler reaction and acid-promoted dihydropyran formation were effective for the stereocontrolled construction of the tetracyclic framework of 1. Starting from known materials, (-)-citrifelin A was synthesized in an eight-step longest linear sequence (LLS) with an overall yield of 17%.

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Authors

Kazuki Hori

Miyu Saito

Karen Shigeta

Journals

Organic Letters

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Institutions

Hoshi University

Ebara (Japan)

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Enantioselective Total Synthesis of Citrifelin A via the Oxa-Pictet–Spengler Reaction and Acid-Promoted Dihydropyran Formation

Key Points

Abstract

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Authors

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Institutions

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