The Use of COP-OAc
in the Catalyst-Controlled Syntheses of 1,3-Polyols

Stefan F. Kirsch; Philipp Klahn; Helge Menz

doi:10.1055/s-0031-1289574

FEATUREARTICLE

The Use of COP-OAc in the Catalyst-Controlled Syntheses of 1,3-Polyols

Stefan F. Kirsch*^a,b, Philipp Klahn^a,b, Helge Menz^a
^a Department Chemie, Technische Universität München, Lichtenbergstr. 4, 85747 Garching, Germany
Fax: +49(89)28913315; e-Mail: stefan.kirsch@ch.tum.de;
^b Bergische Universität Wuppertal, Fachbereich C - Organische Chemie, Gaußstraße 20, 42119 Wuppertal, Germany
e-Mail: sfkirsch@uni-wuppertal.de;

Abstract

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Abstract

An iterative strategy to the 1,3-polyol motif is described. The use of the catalytic asymmetric Overman esterification for the construction of all stereogenic centers is broadly examined as are the sequences to extend the developing polyol chain. The iterative strategies are applied to the total syntheses of rugulactone and polyrhacitides A and B.

1 Introduction

2 Results and Discussion

2.1 Chain Elongation via RCM (Cycle A)

2.2 Total Synthesis of Rugulactone

2.3 Chain Elongation via Ando Olefination (Cycle B) and Total Syntheses of Polyrhacitides A and B

2.4 Useful Variants

3 Conclusions

Key words

polyols - palladium - catalysis - natural products - esters

Full Text

References

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Supplementary Material

Supporting Information