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A Stereospecific Synthesis of Biotin from an Aromatic Precursor. Preliminary Communication

✍ Scribed by Pat N. Confalone; Giacomo Pizzolato; Milan R. Uskoković

Book ID
102250518
Publisher
John Wiley and Sons
Year
1976
Tongue
German
Weight
257 KB
Volume
59
Category
Article
ISSN
0018-019X

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✦ Synopsis

Abstract

The total synthesis of the important natural product biotin 1 from the readily available keto diester 3 is described. This approach features the stereospecific hydrogenation of the thiophene intermediate 19 as the key synthetic step.

The required differentiation of the diacid functionality of compound 7 is achieved by selective lactam formation with the terminal acid to yield the 8‐membered lactam 8. A modified Curtius reaction then affords the rearranged diurethane 18 through a series of acyl transfers. Finally, a novel conversion of the 3, 4‐diurethane moiety to the imidazolidone portion of biotin is utilized to complete the synthesis.

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A Highly Stereoselective Synthesis of C(
A Highly Stereoselective Synthesis of C(11)-Functionalized Aromatic Steroids by an Intramolecular Benzocyclobutene-Olefin -Cycloaddition. Preliminary Communication
✍ Wolfgang Oppolzer; Martin Petrzilka; Kurt Bättig 📂 Article 📅 1977 🏛 John Wiley and Sons 🌐 German ⚖ 246 KB

## Abstract The racemic __cis__‐__anti__‐__trans__‐steroids **9** to **11** have been synthesized in a highly stereoselective manner starting from 4‐methoxybenzocyclobutene carboxylic acid __via__ the key step **8** → **9**. (__cf. Scheme 2__).