Synthesis of the cyclobutanone core of solanoeclepin A intramolecular allene butenolide photocycloaddition.

نویسندگان

  • Bui T B Hue
  • Jan Dijkink
  • Sanne Kuiper
  • Kimberly K Larson
  • Frank S Guziec
  • Kees Goubitz
  • Jan Fraanje
  • Henk Schenk
  • Jan H van Maarseveen
  • Henk Hiemstra
چکیده

The compact tricyclic substructure of solanoeclepin A containing the cyclobutanone ring was prepared by using as the key step a highly regioselective intramolecular [2 + 2]-photocycloaddition reaction between one of the [small pi]-bonds of an allene and the CC double bond of a butenolide.

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

Photochemistry of allenyl salicylaldehydes.

The intramolecular photocycloaddition of aryl aldehydes containing allene side chains is a versatile reaction as it provides a rapid and efficient access to original complex structures such as 1,3,4-tetrahydro-1,4-epoxy-5-alkylidene-2-benzoxepines 2 and substituted 2-oxa-tricyclo[5.2.2.0] (1,5)undeca-4,8,10-triene-9-carbaldehydes 3. Novel polycyclic structures are characterized, and optimized s...

متن کامل

Rh(I)-catalyzed intramolecular [3 + 2] cycloaddition reactions of 1-ene-, 1-yne- and 1-allene-vinylcyclopropanes.

New Rh(I)-catalyzed intramolecular [3 + 2] cycloaddition reactions of 1-ene-, 1-yne and 1-allene-vinylcyclopropanes have been developed, affording an efficient and versatile synthesis of cyclopentane- and cyclopentene-embedded bicyclic structures.

متن کامل

A diastereoselective carbocyclisation of allene-hydrazones through the intramolecular allylic transfer reaction.

A diastereoselective synthesis of cyclic hydrazines was achieved from a carbocyclisation of allene-hydrazones by the Pd-catalyzed distannylation of an allene moiety, followed by the transmetallation of allylic stannane intermediates with TiCl4.

متن کامل

A convergent total synthesis of ouabagenin.

A convergent total synthesis of ouabagenin, an aglycon of cardenolide glycoside ouabain, was achieved by assembly of the AB-ring, D-ring and butenolide moieties. The multiply oxygenated cis-decalin structure of the AB-ring was constructed from (R)-perillaldehyde through the Diels-Alder reaction and sequential oxidations. The intermolecular acetal formation of the AB-ring and D-ring fragments, a...

متن کامل

Total synthesis of brasoside and littoralisone.

The first total syntheses of littoralisone (1) and brasoside (2) have been achieved in 13 overall steps. Both natural products are forged from a common intermediate which is rapidly assembled using organocatalytic technology, including a proline-catalyzed alpha-aminoxylation and a contra-thermodynamic intramolecular Michael addition. Application of the two-step carbohydrate synthesis technology...

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 & biomolecular chemistry

دوره 1 24  شماره 

صفحات  -

تاریخ انتشار 2003