Synthesis of the C1-C13 fragment of leucascandrolide A.

نویسندگان

  • M T Crimmins
  • C A Carroll
  • B W King
چکیده

[reaction: see text] The synthesis of the C1-C13 fragment 3 of leucascandrolide A has been completed utilizing a stereoselective and regioselective reductive cleavage of a highly functionalized spiroketal to incorporate the cis-2,6-disubstituted tetrahydropyan. The spiroketal was constructed by addition of a lithiated pyrone 5 to aldehyde 6.

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

Total synthesis of phoslactomycin A.

A convergent total synthesis of the PP2A-inhibitor phoslactomycin A was achieved using a CuTC-mediated coupling of an alkenyl iodide C1-C13 fragment with an C14-C21 alkenyl stannane in the presence of a protected phosphate. Key features for the assembly of the C1-C13 fragment were an asymmetric dihydroxylation, an Evans-Aldol reaction, and a well-balanced protective group strategy. An asymmetri...

متن کامل

Enantioselective synthesis of oasomycin A, part III: fragment assembly and confirmation of structure.

Herein we address the total synthesis of the natural product oasomycin A by assembly of the C1–C12, C13–C28, and C29–C46 subunits, whose syntheses have been described in the preceding Communications. The synthesis plan (Scheme 1) incorporates a speculative late-stage macrolactonization of the linear seco acid precursor to form a 42-membered lactone that upon global deprotection would provide th...

متن کامل

Tetrafibricin: synthesis of the C1-C13, C15-C25, and C27-C40 fragments.

[structure: see text] A sequence of chemoselective cross-metathesis reactions and enantioselective allyltitanations of aldehydes has been used to prepare the C1-C13, C15-C26, and C27-C40 fragments of tetrafibricin.

متن کامل

A strategy toward the synthesis of C13-oxidized cembrenolides.

An efficient strategy for the construction of C13-oxidized cembrenolides is reported. Central to this strategy is the installation of the C13 hydroxyl group prior to cembrane macrocyclization (via formation of the C1-C2 bond), allowing access to both C13 alcohol epimers. The orientation of the C13 alcohol was found to influence the cyclization mode of the cembranolide scaffold upon furan oxidat...

متن کامل

Stereocontrolled and convergent total synthesis of amphidinolide T3.

Stereocontrolled and convergent total synthesis of amphidinolide T3 has been described. A retrosynthetic scheme was constructed that led to the recognition of readily available and enantiomerically related compounds as starting materials for the total synthesis of amphidinolide T3. Thus, the two key building blocks 6 and 7 were defined as subtargets and synthesized in optically active forms. Th...

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 2 5  شماره 

صفحات  -

تاریخ انتشار 2000