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Stereoselective synthesis of alcohols, XXXI: Stereoselective CC bond formation using chiralZ-pentenylboronates

✍ Scribed by Hoffmann, Reinhard W. ;Ditrich, Klaus ;Köster, Gerhard ;Stürmer, Rainer

Publisher
Wiley (John Wiley & Sons)
Year
1989
Tongue
English
Weight
719 KB
Volume
122
Category
Article
ISSN
0009-2940

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✦ Synopsis

Chirality, transfer of / Diastereoselectivity, reagent control of / Invictolide / Allylboronates / Homoallyl alcohols Using 1,2-dicyclohexyl-1,2-ethanediol as chiral auxiliary, the enantiomerically pure 2-pentenylboronate 9c was obtained. Its addition to benzaldehyde proceeded with complete transfer of chirality to give the syn-E-homoallyl alcohol 11. The ability of the reagent 9c to create new stereocenters under reagent control of diastereoselectivity was tested in its addition to the chiral aldehydes 15 and 24. This resulted in a short and stereospecific synthesis of invictolide (18), as well as of a C-9/C-15-partial structure 25 of erythronolide A.

One strategy for the synthesis of natural products of polyketide-derived biogenesis, especially for the synthesis of polypropionate molecules2), consists in an iterative sequence of chain elongation steps.

📜 SIMILAR VOLUMES

Stereoselective Synthesis of Alcohols, L
Stereoselective Synthesis of Alcohols, L. Stereoselective Synthesis of a C-15/C-27 Segment of the Venturicidines
✍ Hoffmann, Reinhard W. ;Rolle, Ulrike ;Göttlich, Richard 📂 Article 📅 1996 🏛 John Wiley and Sons 🌐 English ⚖ 946 KB

## Abstract Chain extension of an aldehyde by two “propionate” units has been attained by stereoselective allylboration with the chiral 1‐methylbutenyl boronate 3 to give, e.g., the homoallylic alcohol 6, followed by a regioselective hydroboration/carbonylation procedure to give, e.g., the epimeric