A Model Study for Constructing the DEF-Benzoxocin Ring System of Menogaril and Nogalamycin via a Reductive Heck Cyclization

2012 ◽  
Vol 14 (8) ◽  
pp. 1962-1965 ◽  
Author(s):  
Ruogu Peng ◽  
Michael S. VanNieuwenhze
Keyword(s):  
Ring System ◽  
Heck Cyclization ◽  
Model Study

ChemInform Abstract: MODEL STUDY FOR SYNTHESIS OF THE CYTOCHALASIN D CYCLOUNDECANONE RING SYSTEM

1983 ◽  
Vol 14 (11) ◽  
Author(s):  
E. VEDEJS ◽  
M. J. ARNOST ◽  
J. M. EUSTACHE ◽  
G. A. KRAFFT
Keyword(s):  
Ring System ◽  
Cytochalasin D ◽  
Abstract Model ◽  
Model Study

scholarly journals Sequential ring-closing metathesis–vinyl halide Heck cyclization reactions: access to the tetracyclic ring system of ervitsine

Tetrahedron ◽  
2012 ◽  
Vol 68 (24) ◽  
pp. 4641-4648 ◽  
Author(s):  
M.-Lluïsa Bennasar ◽  
Ester Zulaica ◽  
Daniel Solé ◽  
Sandra Alonso
Keyword(s):  
Ring System ◽  
Cyclization Reactions ◽  
Ring Closing Metathesis ◽  
Heck Cyclization ◽  
Vinyl Halide

Model Study for a General Approach to Morphine and Noroxymorphone via a Rare Heck Cyclization

1999 ◽  
Vol 1 (13) ◽  
pp. 2085-2087 ◽  
Author(s):  
Dean A. Frey ◽  
Caiming Duan ◽  
Tomas Hudlicky
Keyword(s):  
Heck Cyclization ◽  
Model Study

Model study for synthesis of the cytochalasin D cycloundecanone ring system

1982 ◽  
Vol 47 (22) ◽  
pp. 4384-4386 ◽  
Author(s):  
E. Vedejs ◽  
M. J. Arnost ◽  
J. M. Eustache ◽  
G. A. Krafft
Keyword(s):  
Ring System ◽  
Cytochalasin D ◽  
Model Study

Synthetic Study on Lactonamycins, Part 2: Stereoselective Access to ABCD-Ring System

Synlett ◽  
2020 ◽  
Vol 31 (16) ◽  
pp. 1623-1628
Author(s):  
Keisuke Suzuki ◽  
Hiroshi Takikawa ◽  
Kazuki Murata ◽  
Shogo Sato ◽  
Takuma Kawada ◽  
...  
Keyword(s):  
Total Synthesis ◽  
Hydroxy Group ◽  
Ring Opening ◽  
Ring System ◽  
Model Study ◽  
Viable Approach

Toward a stereoselective total synthesis of the lactonamycins, we recently reported an approach to the DEF-ring system. Here we report a model study for constructing the ABCD-ring system, revealing a viable approach through (1) construction of the C-ring by asymmetric benzoin cyclization, (2) introduction of an angular hydroxy group through oxidation of an isoxazolium salt, and (3) construction of the AB rings through a ring-opening/closing sequence.

Synthetic Study on Acremoxanthone A, Part 2: Model Study on the EFG Xanthone Moiety through a Nitrile Oxide Cycloaddition–SNAr Sequence

Synlett ◽  
2020 ◽  
Author(s):  
Keisuke Suzuki ◽  
Hiroshi Nakakohara ◽  
Yoichi Hirano ◽  
Ken Ohmori ◽  
Hiroshi Takikawa
Keyword(s):  
Total Synthesis ◽  
Ring System ◽  
Nitrile Oxide ◽  
Dipolar Cycloaddition ◽  
Model Study ◽  
Snar Reaction ◽  
F Ring ◽  
Key Steps

AbstractToward a total synthesis of acremoxanthone A, we report a model study on the construction of the EFG ring system. The key steps include (1) an intermolecular 1,3-dipolar cycloaddition of an aryl nitrile oxide with a dienone, and (2) an SNAr reaction for construction of the F ring.

Semipinacol rearrangement of a bicyclo[7.2.0]undecane framework into a bicyclo[6.3.0]undecane skeleton: A model study on the biosynthesis of seiridiasteriscane A

2021 ◽  
Author(s):  
Osamu Ishibashi ◽  
Mami Nishiyama ◽  
Eunsang Kwon ◽  
Masaru Hashimoto ◽  
Shigefumi Kuwahara ◽  
...  
Keyword(s):  
Silica Gel ◽  
Biosynthetic Pathway ◽  
Ring System ◽  
Model Study ◽  
Semipinacol Rearrangement

Abstract Seiridiasteriscane A is an asteriscane-type sesquiterpenoid bearing a trans-fused bicyclo[6.3.0]undecane skeleton. Although its biosynthesis has been proposed to involve a semipinacol rearrangement of a putative intermediary acetate bearing a bicyclo[7.2.0]undecane ring system (presumably derived from co-isolated pestalotiopsin M) followed by epimerization of the resulting cis-fused seiridiasteriscane B, such a type of semipinacol rearrangement has never been reported so far. Our model study revealed that a 1-hydroxybicyclo[7.2.0]undecan-2-yl acetate underwent a smooth and stereospecific semipinacol rearrangement with the assistance of Et2AlCl to give the corresponding bicyclo[6.3.0]undecane-9-one. In addition, the resulting cis-fused 5,8-bicyclic ketone was partially epimerized to the corresponding trans-fused ketone by prolonged adsorption onto a silica gel plate. These results may support a recently proposed biosynthetic pathway of seiridiasteriscane A.

A model study for the total synthesis of (±)-scopadulin: stereoselective construction of the A/B ring system with desired functionalities

Tetrahedron ◽  
2001 ◽  
Vol 57 (1) ◽  
pp. 127-134 ◽  
Author(s):  
S.M. Abdur Rahman ◽  
Hiroaki Ohno ◽  
Hitoshi Yoshino ◽  
Norifumi Satoh ◽  
Mahoto Tsukaguchi ◽  
...  
Keyword(s):  
Total Synthesis ◽  
Ring System ◽  
Model Study

Fusicoccin ring system by [4+4] cycloaddition. 2. A model study

1999 ◽  
Vol 40 (21) ◽  
pp. 4007-4010 ◽  
Author(s):  
Scott McN. Sieburth ◽  
Kevin F. McGee ◽  
Taleb H. Al-Tel
Keyword(s):  
Ring System ◽  
Model Study
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