Ring-Closing Metathesis with Vicinal Dibromoalkenes as Protected Alkynes: A Synthetic Approach to Macrocyclic Enynes.
نویسندگان
چکیده
A new strategy to access macrocyclic enynes was developed. To block undesired ene-yne cyclization pathways, alkynes were protected via bromination and the resultant acyclic vic-(E)-dibromotrienes participated in selective ene-ene ring closing metathesis reactions. Zinc-promoted deprotection of (E)-dibromodienes provided macrocyclic enynes in high yields.
منابع مشابه
Bridgehead vicinal diallylation of norbornene derivatives and extension to propellane derivatives via ring-closing metathesis
Here, we report a simple synthetic strategy to the bridgehead vicinal diallylation of norbornene derivatives. These substrates are useful to generate propellanes via ring-closing metathesis. Single-crystal X-ray diffraction analysis of four compounds led to the realization of configurational correction of earlier reported molecules.
متن کاملSelf‐Assembly of Disorazole C1 through a One‐Pot Alkyne Metathesis Homodimerization Strategy†
Alkyne metathesis is increasingly explored as a reliable method to close macrocyclic rings, but there are no prior examples of an alkyne-metathesis-based homodimerization approach to natural products. In this approach to the cytotoxic C2-symmetric marine-derived bis(lactone) disorazole C1, a highly convergent, modular strategy is employed featuring cyclization through an ambitious one-pot alkyn...
متن کاملA short route for the synthesis of "sweet" macrocycles via a click-dimerization-ring-closing metathesis approach.
A facile and flexible approach for the preparation of macrocyclic molecules containing different carbohydrate moieties is presented, employing the reaction cascade: click-dimerization and ring-closing metathesis.
متن کاملStereoselective synthesis of (-)-spicigerolide.
(-)-Spicigerolide was stereoselectively synthesized from a protected (S)-lactaldehyde. The synthesis of the polyacetylated framework relied on two Zn-mediated stereoselective additions of alkynes to aldehydes as well as a regiocontrolled [3,3]-sigmatropic rearrangement of an allylic acetate. The pyranone moiety was constructed via ring-closing metathesis.
متن کاملThe joy and challenge of small rings metathesis.
Recent decades have seen a burgeoning of interest in olefin metathesis, as witnessed by a rapidly growing number of elegant applications. Using this tool, chemists can now efficiently synthesize an impressive range of molecules that only a decade ago required significantly longer and tedious routes.[1] Several types of olefin metathesis have been identified so far, among them ring-closing metat...
متن کاملذخیره در منابع من
با ذخیره ی این منبع در منابع من، دسترسی به آن را برای استفاده های بعدی آسان تر کنید
برای دانلود متن کامل این مقاله و بیش از 32 میلیون مقاله دیگر ابتدا ثبت نام کنید
ثبت ناماگر عضو سایت هستید لطفا وارد حساب کاربری خود شوید
ورودعنوان ژورنال:
- Organic letters
دوره 17 21 شماره
صفحات -
تاریخ انتشار 2015