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Protolytic Opening of Two Diastereoisomeric Cyclopropanols

✍ Scribed by Peter Schönholzer; Terence S. Wan; Albert Fischli

Publisher
John Wiley and Sons
Year
1984
Tongue
German
Weight
288 KB
Volume
67
Category
Article
ISSN
0018-019X

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✦ Synopsis

Abstract

Cob(I) alamin (1(I))‐catalyzed reduction of the aldehyde 2 led to the two crystalline cyclopropanols 3 and 4 (see Scheme 2). The protolytic ring‐opening starting from 3 produced the saturated aldehydes 6 and 7;8 was formed in traces only (see Scheme 3). The protolysis starting from 3 led, therefore, mainly to retention of configuration at the spiro C‐atom (7); ring‐opening with inversion was observed in traces only (8). Starting from 4, the protolysis produced 9 and 7; the absence of 8 showed this protolysis to proceed 9 and 7; the absence of 8 showed this protolysis to proceed exclusively with inversion of configuration at the spiro center. Of the p‐bromobenzoate 5 (cf. Scheme 2) the structure has been determined by X‐ray analysis.

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Preparation of Two Diastereoisomeric Dec
Preparation of Two Diastereoisomeric Decalin Synthons and (−)-Ambrox
✍ Yi-Peng Xie; Bo-Gang Li; Ying-Gang Luo; Xiao-Zhen Chen; Guo-Lin Zhang 📂 Article 📅 2008 🏛 John Wiley and Sons 🌐 German ⚖ 188 KB

## Abstract Two diastereoisomeric decalins, (2__S__,4a__S__,5__S__,6__R__)‐ and (2__S__,4a__S__,5__R__,6__R__)‐5‐(2‐hydroxyethyl)‐1,1,4a,6‐tetramethyldecalin‐2,6‐diol (**5** and **6**) were prepared from the degradation products of oleanolic acid. Starting from **6**, (−)‐ambrox (**4**) was synthes