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Synthesis 2001(5): 0671-0689
DOI: 10.1055/s-2001-12757
REVIEW
© Georg Thieme Verlag Stuttgart · New York

Total Synthesis of Bakkanes

, Jr. Luiz F. Silva
Instituto de Química, Universidade de São Paulo, C.P. 26077, 05513-970 - São Paulo - SP, Brazil
e-Mail: luizfsilvajr@hotmail.com;
Further Information

Publication History

Received 2 January 2001
Publication Date:
28 September 2004 (online)

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Abstract

A review showing the synthetic efforts toward the syntheses of bakkanes from the first total synthesis in 1973 until the middle of 2000 is presented. Approaches for constructing β-methylene-γ-butyrolactones are also reviewed.

  • 1 Introduction

  • 2 Construction of β-Methylene-γ-butyrolactones

  • 2.1 β-Methylene-γ-butyrolactones

  • 2.2 α-Spiro-β-methylene-γ-butyrolactones

  • 3 Total Syntheses of Bakkanes

  • 3.1 Strategies used in the Total Syntheses of Bakkanes

  • 3.2 Syntheses of Bakkenolide-A

  • 3.2.1 Evans’ Synthesis

  • 3.2.2 Greene’s Syntheses

  • 3.2.3 Hayashi’s Synthesis

  • 3.2.4 Petragnani’s Synthesis

  • 3.2.5 Back’s Synthesis

  • 3.3 Syntheses of Homogynolide-A

  • 3.3.1 Greene’s Syntheses

  • 3.3.2 Mori’s Synthesis

  • 3.3.3 Srikrishna’s Synthesis

  • 3.4 Syntheses of Homogynolide-B

  • 3.4.1 Greene’s Synthesis

  • 3.4.2 Srikrishna’s Synthesis

  • 3.5 Synthesis of Palmosalide-C

  • 3.5.1 Greene’s Synthesis

  • 3.6 Syntheses of 9-Acetoxyfukinanolide

  • 3.6.1 Greene’s Syntheses

  • 4 Conclusion

Key words

total synthesis - natural products - bakkanes - bakkenolides - β-methylene-γ-butyrolactone

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Petragnani N., Silva G. V. J.; unpublished results.