Abstract

A conceptually new and scalable strategy (ten linear steps, 13.9% overall yield) has been developed to synthesize (+)-7-deoxy­pancratistatin from optically pure 7-azabicyclo[2.2.1]heptanone scaffold. The crucial trans-B–C ring junction was fixed at an early stage of the synthesis by exploiting the rigid bicyclic structural framework of the starting precursor. Stereoselective installation of hydroxyl groups around the perimeter of the cyclohexenyl C-ring involved sequential epoxidation–phenylselenylation–oxydeselenylation sequence followed by dihydroxylation. The most attractive feature of this synthesis is the use of a protection–deprotection step only at the penultimate step making the protocol very efficient and atom economical.

A conceptually new and scalable strategy (ten linear steps, 13.9% overall yield) has been developed to synthesize (+)-7-deoxy­pancratistatin from optically pure 7-azabicyclo[2.2.1]heptanone scaffold. The crucial trans-B–C ring junction was fixed at an early stage of the synthesis by exploiting the rigid bicyclic structural framework of the starting precursor. Stereoselective installation of hydroxyl groups around the perimeter of the cyclohexenyl C-ring involved sequential epoxidation–phenylselenylation–oxydeselenylation sequence followed by dihydroxylation. The most attractive feature of this synthesis is the use of a protection–deprotection step only at the penultimate step making the protocol very efficient and atom economical.

中文翻译：

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从对映体纯的7-氮杂双环[2.2.1]庚酮骨架上可扩展合成芳樟科异卡西替利生物碱：（+）-7-脱氧潘克拉汀的全合成

摘要

已开发出一种概念上新颖且可扩展的策略（十个线性步骤，总产率为13.9％），以从光学纯的7-氮杂双环[2.2.1]庚酮骨架中合成（+）-7-脱氧潘克拉汀。通过利用起始前体的刚性双环结构框架，关键的反式-B-C环连接固定在合成的早期。围绕环己烯基C环的周边立体选择性安装羟基涉及顺序环氧化-苯硒基化-氧去硒基化顺序，然后进行二羟基化。该合成法最吸引人的特点是仅在倒数第二步使用保护-脱保护步骤，从而使该协议非常有效且经济实惠。

已开发出一种概念上新颖且可扩展的策略（十个线性步骤，总产率为13.9％），以从光学纯的7-氮杂双环[2.2.1]庚酮骨架中合成（+）-7-脱氧潘克拉汀。通过利用起始前体的刚性双环结构框架，关键的反式-B-C环连接固定在合成的早期。围绕环己烯基C环的周边立体选择性安装羟基涉及顺序环氧化-苯硒基化-氧去硒基化顺序，然后进行二羟基化。该合成法最吸引人的特点是仅在倒数第二步使用保护-脱保护步骤，从而使该协议非常有效且经济实惠。