Biomimetic total synthesis of (±)-yezo'otogirin A

2014 ◽  
Vol 12 (16) ◽  
pp. 2519-2522 ◽  
Author(s):  
Hiu C. Lam ◽  
Kevin K. W. Kuan ◽  
Jonathan H. George
Keyword(s):  
Total Synthesis ◽  
Late Stage ◽  
Radical Cyclization ◽  
Biosynthetic Precursor ◽  
Oxidative Radical Cyclization

A concise total synthesis of (±)-yezo'otogirin A has been achieved via its presumed biosynthetic precursor using a late-stage biomimetic oxidative radical cyclization.

Peroxide-Mediated Oxidative Radical Cyclization to the Quinazolinone System: Efficient Syntheses of Deoxyvasicinone, Mackinazolinone and (±)-Leucomidine C

Synthesis ◽  
2020 ◽  
Author(s):  
Luis D. Miranda ◽  
Jazmín García-Ramírez
Keyword(s):  
Natural Products ◽  
Free Radical ◽  
Total Synthesis ◽  
Radical Cyclization ◽  
Oxidative Cyclization ◽  
Dicumyl Peroxide ◽  
Cyclization Process ◽  
Radical Cascade ◽  
Oxidative Radical Cyclization

AbstractAn efficient protocol for obtaining fused quinazolinones through an oxidative free-radical cyclization under metal- and tin-free conditions is described. The oxidative cyclization of various N-3-ω-iodoalkyl derivatives to provide tricyclic systems using dicumyl peroxide as the sole reagent is studied. The method then is employed for the syntheses of 5-, 6-, and 7-membered fused quinazolinone analogues, including the natural products deoxyvasicinone and mackinazolinone. A xanthate-based oxidative radical cascade addition/cyclization process that allows the production of new menthol- and testosterone-quinazolinone conjugates, as well as the first total synthesis of leucomidine C, are also reported.

Total Synthesis of 7,11-Cyclobotryococca-5,12,26-triene Using an Oxidative Radical Cyclization as a Key Step

2010 ◽  
Vol 12 (12) ◽  
pp. 2738-2741 ◽  
Author(s):  
Justin J. Davies ◽  
Thomas M. Krulle ◽  
Jonathan W. Burton
Keyword(s):  
Total Synthesis ◽  
Radical Cyclization ◽  
Oxidative Radical Cyclization

Convergent Total Synthesis of Principinol D, a Rearranged Kaurane Diterpenoid

2019 ◽  
Author(s):  
Timothy Newhouse ◽  
Aneta Turlik ◽  
Yifeng Chen ◽  
Anthony Scruse
Keyword(s):  
Total Synthesis ◽  
Natural Product ◽  
Late Stage ◽  
Membered Ring ◽  
Entry Point ◽  
Ketone Reduction ◽  
Coupling Approach

<div> <p>The total synthesis of principinol D, a rearranged kaurane diterpenoid, is reported. This grayanane natural product is constructed via a convergent fragment coupling approach, wherein the central 7-membered ring is synthesized at a late stage. The bicyclo[3.2.1]octane fragment is accessed by a Ni-catalyzed α-vinylation reaction. Strategic reductions include a diastereoselective SmI<sub>2</sub>-mediated ketone reduction with PhSH and a new protocol for selective ester reduction in the presence of ketones. The convergent strategy reported herein may be an entry point to the larger class of kaurane diterpenoids.</p> </div>

The Total Synthesis of Rhabdastrellic Acid A

2018 ◽  
Author(s):  
Yaroslav Boyko ◽  
Christopher Huck ◽  
David Sarlah
Keyword(s):  
Total Synthesis ◽  
Late Stage ◽  
Cross Coupling ◽  
Side Chains ◽  
General Strategy ◽  
Modular Approach ◽  
Linear Sequence ◽  
Generating Sequence ◽  
First Time

<div>The first total synthesis of rhabdastrellic acid A, a highly cytotoxic isomalabaricane triterpenoid, has been accomplished in a linear sequence of 14 steps from commercial geranylacetone. The prominently strained <i>trans-syn-trans</i>-perhydrobenz[<i>e</i>]indene core characteristic of the isomalabaricanes is efficiently accessed in a selective manner for the first time through a rapid, complexity-generating sequence incorporating a reductive radical polyene cyclization, an unprecedented oxidative Rautenstrauch cycloisomerization, and umpolung 𝛼-substitution of a <i>p</i>-toluenesulfonylhydrazone with in situ reductive transposition. A late-stage cross-coupling in concert with a modular approach to polyunsaturated side chains renders this a general strategy for the synthesis of numerous family members of these synthetically challenging and hitherto inaccessible marine triterpenoids.</div>

ChemInform Abstract: Total Synthesis of (-)-γ-Lycorane Using Diastereoselective 5-endo-trig Radical Cyclization of N-Vinylic α-Halo Amides.

ChemInform ◽  
2010 ◽  
Vol 30 (13) ◽  
pp. no-no
Author(s):  
Masazumi Ikeda ◽  
Shinji Ohtani ◽  
Tatsunori Sato ◽  
Hiroyuki Ishibashi
Keyword(s):  
Total Synthesis ◽  
Radical Cyclization

scholarly journals Stereocontrolled total synthesis of (+)-vinblastine

2003 ◽  
Vol 75 (1) ◽  
pp. 29-38 ◽  
Author(s):  
Satoshi Yokoshima ◽  
T. Ueda ◽  
S. Kobayashi ◽  
A. Sato ◽  
Takeshi Kuboyama ◽  
...  
Keyword(s):  
Total Synthesis ◽  
Coupling Reaction ◽  
Radical Cyclization ◽  
Critical Coupling ◽  
Efficient Manner ◽  
Complete Control ◽  
Highly Efficient ◽  
Indole Synthesis

Stereocontrolled total synthesis of (+)-vinblastine (1) has been achieved using a novel radical-mediated indole synthesis developed in our laboratories. The isothiocyanate 18, prepared readily from quinoline 17, underwent a facile addition of the malonate anion to give 19. The o-alkenylthioanilide 19 was then converted to indole 20 by radical cyclization and protection. (−)-Vindoline (2) was prepared from this key intermediate 20 in a highly efficient manner. The indole core of the 11-membered intermediate 3 was constructed similarly from quinoline. The critical coupling reaction between 2 and the chloroindolenine derived from 3 proceeded with complete control of stereochemistry to give the desired product 66 in 97 % yield, which could be successfully converted to (+)-vinblastine (1).

scholarly journals Back Cover: Total Synthesis of (−)‐Salinosporamide A via a Late Stage C−H Insertion (Angew. Chem. Int. Ed. 30/2019)

2019 ◽  
Vol 58 (30) ◽  
pp. 10376-10376
Author(s):  
Hadi Gholami ◽  
Aman Kulshrestha ◽  
Olivia K. Favor ◽  
Richard J. Staples ◽  
Babak Borhan
Keyword(s):  
Total Synthesis ◽  
Late Stage ◽  
Back Cover ◽  
Salinosporamide A
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