Efficient Asymmetric Synthesis of abeo-Abietane-Type Diterpenoids by Using the Intramolecular Heck Reaction
- Manabu Node
- ,
- Minoru Ozeki
- ,
- Loïc Planas
- ,
- Masashi Nakano
- ,
- Hirofumi Takita
- ,
- Daisuke Mori
- ,
- Shinji Tamatani
- , and
- Tetsuya Kajimoto
Abstract
The synthesis of the abeo-abietane-type diterpenoids, i.e., (−)-dichroanal B, (−)-dichroanone, and taiwaniaquinone H, was achieved by using the intramolecular asymmetric Heck reaction. Our synthetic routes required fewer steps and gave a much higher overall yield and ee within shorter steps than those for racemic and antipodal forms reported to date (10, 12, and 13 steps with an overall yield of 50%, 40%, and 39%, and 94%, 98%, and 98% ee, respectively).
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