Carotenoids and related polyenes, part 12. First total synthesis and absolute configuration of 3'-deoxycapsanthin and 3,4-didehydroxy-3'-deoxycapsanthin |
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Authors: | Yamano Yumiko Chary Mahankhali Venu Wada Akimori |
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Affiliation: | Department of Organic Chemistry for Life Science, Kobe Pharmaceutical University, Japan. y-yamano@kobepharma-u.ac.jp |
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Abstract: | The synthesis of 3'-deoxycapsanthin (1) and 3,4-didehydroxy-3'-deoxycapsanthin (2), carotenoids of paprika, has been achieved by employing Lewis acid-promoted regio- and stereoselective rearrangement of the C(15)-epoxy dienal 5a. The absolute stereochemistry of the newly formed C-5 chiral center of rearrangement product 6a was determined to be (R) from its alternative synthesis derived from (+)-(R)-camphonanic acid (11). |
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