Stereoselective total synthesis of (-)-kumausallene.

نویسندگان

  • Jenny B Werness
  • Weiping Tang
چکیده

A stereoselective total synthesis of (-)-kumausallene was completed in 12 steps from acetylacetone. The hidden symmetry of (-)-kumausallene was recognized, and its skeleton was constructed efficiently from a C(2)-symmetric diol by a palladium-catalyzed cascade reaction. High diastereoselectivity was observed for the DMF-promoted biomimetic 1,4-bromocyclization of a conjugated enyne.

برای دانلود متن کامل این مقاله و بیش از 32 میلیون مقاله دیگر ابتدا ثبت نام کنید

ثبت نام

اگر عضو سایت هستید لطفا وارد حساب کاربری خود شوید

منابع مشابه

STEREOSELECTIVE SYNTHESIS OF METHYL TETRA-0-METHYL a-AND P-D-GLUCO-AND MANNOPYRANOSIDES

Methyl tetra - 0-methyl- ?-D- glucopyranoside is stereoselectively prepared from tetramethyl-D- glucopyranose by using (MeI+NaH) in toluene (86%) or cyclohexane (85%), while its ?- isomer is best synthesized in hexamethyl phosphoramide (64%). Similarly, methyl tetra-o-methyl-?- D-mannopyranoside is synthesized in cyclohexane (80%), while its ?- isomer is predominantly prepared by (MeI+n-Bu...

متن کامل

The first stereoselective total synthesis of quinine.

The first entirely stereoselective total synthesis of (-)-quinine is reported.

متن کامل

The first stereoselective total synthesis of neosemburin and isoneosemburin.

The Claisen rearrangement of sugar derived allyl vinyl ether, Wittig olefination and intramolecular acetalization reactions were used as key steps in the first stereoselective total synthesis of neosemburin and isoneosemburin through the formation of a 3-C-branched sugar precursor as a key intermediate.

متن کامل

Stereoselective total synthesis of (-)-cleistenolide.

A facile stereoselective total synthesis of cleistenolide (1) from the natural chiral template d-arabinose has been achieved in eight steps and 49% overall yield, employing key steps including Wittig olefination, selective 1,3-trans-acetal formation, and modified Yamaguchi esterification.

متن کامل

A stereoselective total synthesis of 7,8-O-isopropylidene iriomoteolide-3a.

A stereoselective total synthesis of 7,8-O-isopropylidene iriomoteolide-3a has been achieved by using Yamaguchi esterification, Julia-Kocienski olefination, organocatalytic α-oxidation, and ring-closing metathesis reaction as key bond-forming steps.

متن کامل

ذخیره 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 نام

اگر عضو سایت هستید لطفا وارد حساب کاربری خود شوید

عنوان ژورنال:
  • Organic letters

دوره 13 14  شماره 

صفحات  -

تاریخ انتشار 2011