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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.


📜 SIMILAR VOLUMES


An enantiospecific synthesis of (−)-tala
✍ Isidoro Izquierdo Cubero; Maria T. Plaza Lo´pez-Espinosa 📂 Article 📅 1990 🏛 Elsevier Science 🌐 English ⚖ 833 KB

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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