Asymmetric induction by sulfinyl chirality. A total synthesis of (+)-talaromycin A and (−)-talaromycin B
✍ Scribed by Chuzo Iwata; Masahiro Fujita; Yasunori Moritani; Kohji Hattori; Takeshi Imanishi
- Book ID
- 104227722
- Publisher
- Elsevier Science
- Year
- 1987
- Tongue
- French
- Weight
- 262 KB
- Volume
- 28
- Category
- Article
- ISSN
- 0040-4039
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✦ Synopsis
A total synthesis of (+)-talaromycin A and (-)talaromycin B was accomplished by means of successive asymmetric induction of all chiral centers using a chiral sulfinyl group.
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3R,4R,5S,6R,9RS)-9-Ethyl-3,4,5-trihydroxy-l,7-dioxaspiro[5.5]undecane (9) has been synthesised from 2,3:4,5-di-0-isopropylidene-/I-D-fructopyranose (3) and transformed into (-)-talaromycin A (1). (-)-Talaromycin B (2) was obtained by isomerisation of 1 in acid medium. \* Dedicated to Professor Lesli
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