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. 2005 Feb 17;7(4):741-4.
doi: 10.1021/ol050017s.

Total synthesis of natural (+)- [corrected] and ent-(-)-4-desacetoxy-6,7-dihydrovindorosine [corrected] and natural and ent-minovine: oxadiazole tandem intramolecular Diels-Alder/1,3-dipolar cycloaddition reaction

Zhong Qing Yuan  1 , Hayato Ishikawa, Dale L Boger
Affiliations

Total synthesis of natural (+)- [corrected] and ent-(-)-4-desacetoxy-6,7-dihydrovindorosine [corrected] and natural and ent-minovine: oxadiazole tandem intramolecular Diels-Alder/1,3-dipolar cycloaddition reaction

Zhong Qing Yuan et al. Org Lett. .

Erratum in

  • Org Lett. 2005 May 12;7(10):2079

Abstract

Efficient and unusually concise total syntheses of both enantiomers of the Aspidosperma alkaloids 4-desacetoxy-6,7-dihydrovindorosine (12) and minovine (1) are detailed. A tandem intramolecular Diels-Alder/1,3-dipolar cycloaddition reaction of the 1,3,4-oxadiazole 8, in which three new rings, four new C-C bonds, and five stereocenters are formed, is a key step in the sequence. The availability of optically active material permitted an assessment of the enantiomeric integrity of minovine and the source of its reported unusual optical rotation. [Reaction: see text]

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Figures

Figure 1
Figure 1
Tandem intramolecular [4 + 2]/[3 + 2] cycloaddition reactions of a 1,3,4-oxadiazole
Figure 2
Figure 2
X-ray ORTEP of 12
Scheme 1
Scheme 1
Preparation of 1,3,4-oxadiazole 6
Scheme 2
Scheme 2
Synthesis of 4-desacetoxy-6,7-dihydrovindorosine and minovine
Scheme 3
Scheme 3
Desulfurization and reductive oxido-bridge opening
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