Unravelling Photochemical Relationships Among Natural Products from Aplysia dactylomela
نویسندگان
چکیده
Aplydactone (1) is a brominated ladderane sesquiterpenoid that was isolated from the sea hare Aplysia dactylomela together with the chamigranes dactylone (2) and 10-epi-dactylone (3). Given the habitat of A. dactylomela, it seems likely that 1 is formed from 2 through a photochemical [2 + 2] cycloaddition. Here, we disclose a concise synthesis of 1, 2, and 3 that was guided by excited state theory and relied on several highly stereoselective transformations. Our experiments and calculations confirm the photochemical origin of 1 and explain why it is formed as the sole isomer. Irradiation of 3 with long wavelength UV light resulted in a [2 + 2] cycloaddition that proceeded with opposite regioselectivity. On the basis of this finding, it seems likely that the resulting regioisomer, termed "8-epi-isoaplydactone", could also be found in A. dactylomela.
منابع مشابه
شناسائی ، استخراج و تخلیص پروتئین 60 کیلو دالتونی ماده بنفش رنگ ترشحه از خرگوش دریایی خلیج فارس *Aplysia dactylomela با اثرات ضدسرطانی
خرگوش دریایی از نرمتنان دریایی است که بدلیل داشتن مواد باخواص بیولوژیک باوزن ملکولی کم ، توجه پژوهشگران را به خود معطوف داشته است . این نرم تن ماده ای بنفش رنگ جهت دفاع از خود آزاد می سازد که به نظر می رسد حاوی ترکیبات باپتانسیل ضد نئوپلاستیک باشد. برای خالص سازی پروتئین 60 کیلودالتونی موجود در ماده بنفش رنگ خرگوش دریایی Aplysia dactylomela خلیج فارس ، از تکنیک های تغلیظ پروتئین باسولفات آمون...
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عنوان ژورنال:
دوره 3 شماره
صفحات -
تاریخ انتشار 2017