Pisiferic acid synthesis transannular oxidation

Matsumoto and Usui [8] reported the first total synthesis of ( )-pisiferic acid (1) and ( )-methylpisiferate (3) and this is depicted in Fig. (2). In this synthesis the fundamental skeleton of pisiferic acid has been constructed by the cyclization of enone (9). The introduction of C-10 carboxylic acid in pisiferic acid was accomplished by transannular oxidation. The depicted synthesis has been divided in two parts, Fig. (2) describes the preparation of the alcohol (17) and Fig. (3) deals with the conversion of the alcohol (17) to pisiferic acid (1). 

In the present synthesis, the preparation of two cyclic ethers (31) and (41) and their transformations to pisiferic acid (1) are described. In this synthesis, the introduction of carboxylic acid at angular position has been accomplished by transannular oxidation. 

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See also in sourсe #XX -- [ , ]

See also in sourсe #XX -- [ , ]

See also in sourсe #XX -- [ , , ]

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