Total synthesis of Periplanone B by W.C. Still (1979)

Presented by:Md Shafaat Al Mehedi

Nicolaou, K.C.; Sorensen, E.J. Classics in Total Synthesis, Targets, Strategies, Methods; Wiley-VCH: New York, 1996; pp 211-220.Still, W.C. J. Am. Chem. Soc. 1979, 101(9), 2493 1

History

• Activity of a potent sex pheromone in female American cockroaches ofthe species Periplaneta americana reported in 1952. Isolation of activecompounds was difficult as individual cockroaches store less than 1 g.

• Isolation of two extremely active constituents of the sex pheromone,Periplanones A & B by Persoons et al in 1976. Periplanone B was presentin relatively larger measure than A.

• First total synthesis of Periplanone B by W.C. Still was reported in 1979with relative stereochemistry. Later in the same volume of that paper,absolute stereochemistry of the molecule was also described by W.C.Still and C.J. Persoons.

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Retrosynthetic analysis of Periplanone B

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Retrosynthetic analysis of Periplanone B

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Synthesis of Key intermediate 2

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Synthesis of Key intermediate 2

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Synthesis of Key intermediate 2

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Synthesis of Key intermediate 2

8J. Org. Chem. 1987, 52, 954-955

Strategy of Synthesis of different diastereomers of Periplanone B

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Synthesis of isomer 14

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Synthesis of isomer 14

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Still, W.C. J. Am. Chem. Soc. 1979, 101(9), 2493

Synthesis of isomer 14

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J. Am. Chem. Soc. 1965, 87, 1353

Synthesis of isomer 17

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Synthesis of isomer 17

14Comprehensive Organic Name Reactions and Reagents, 2010, 2176-2187

Synthesis of isomer 17

15J. Am. Chem. Soc. 1973, 95, 6136

Synthesis of Periplanone-B

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