Total synthesis of the potent antifungal agents bengazole C and E

2009 ◽  
Vol 74 (6) ◽  
pp. 887-900 ◽  
Author(s):  
Álvaro Enríquez-García ◽  
Steven V. Ley
Keyword(s):  
Natural Products ◽  
Antifungal Activity ◽  
Total Synthesis ◽  
Marine Natural Products ◽  
Antifungal Agents ◽  
Nitrile Oxide ◽  
Total Syntheses ◽  
Unique Structure

The bengazoles are marine natural products with unique structure, containing two oxazole rings flanking a single carbon. They show very potent antifungal activity. The total syntheses of bengazole C and E are described following a convergent route which involves diastereoselective cycloaddition of an appropriately substituted nitrile oxide with a butane-1,2-diacetal-protected alkenediol as the key step.

Total synthesis of bryostatin 3

Science ◽  
2020 ◽  
Vol 368 (6494) ◽  
pp. 1007-1011 ◽  
Author(s):  
Barry M. Trost ◽  
Youliang Wang ◽  
Andreas K. Buckl ◽  
Zhongxing Huang ◽  
Minh H. Nguyen ◽  
...  
Keyword(s):  
Natural Products ◽  
Total Synthesis ◽  
Marine Natural Products ◽  
Biological Activities ◽  
Step Count ◽  
Total Syntheses ◽  
Linear Sequence ◽  
Wide Range

Bryostatins are a family of 21 complex marine natural products with a wide range of potent biological activities. Among all the 21 bryostatins, bryostatin 3 is structurally the most complex. Whereas nine total syntheses of bryostatins have been achieved to date, bryostatin 3 has only been targeted once and required the highest number of steps to synthesize (43 steps in the longest linear sequence and 88 total steps). Here, we report a concise total synthesis of bryostatin 3 using 22 steps in the longest linear sequence and 31 total steps through a highly convergent synthetic plan by the use of highly atom-economical and chemoselective transformations in which alkynes played a major role in reducing step count.

Enantioselective Total Syntheses of Marine Natural Products (+)-Cylindricines C, D, E and Their Diastereomers

2021 ◽  
Author(s):  
Ying-Hong Huang ◽  
Zhan-Jiang Liu ◽  
Pei-Qiang Huang
Keyword(s):  
Natural Products ◽  
Total Synthesis ◽  
Marine Natural Products ◽  
Total Syntheses

A seven-step total synthesis of (+)-cylindricine D and epi-cylindricine D is described. The efficiency relies on the highly diastereoselective reductive bis-functionalization of N,O-protected (S)-pyroglutaminol by our recently improved protocol to...

Total synthesis of marine natural products separacenes A and B

2017 ◽  
Vol 15 (22) ◽  
pp. 4842-4850 ◽  
Author(s):  
Subhendu Das ◽  
Rajib Kumar Goswami
Keyword(s):  
Natural Products ◽  
Total Synthesis ◽  
Marine Natural Products

Aryne-based strategy in the total synthesis of naturally occurring polycyclic compounds

2018 ◽  
Vol 47 (21) ◽  
pp. 8030-8056 ◽  
Author(s):  
Hiroshi Takikawa ◽  
Arata Nishii ◽  
Takahiro Sakai ◽  
Keisuke Suzuki
Keyword(s):  
Natural Products ◽  
Total Synthesis ◽  
Polycyclic Compounds ◽  
Total Syntheses ◽  
Naturally Occurring

This review has outlined the strategies and tactics of using arynes in the total syntheses of polycyclic natural products.

ChemInform Abstract: MARINE NATURAL PRODUCTS FROM THE ATLANTIC ZONE. PART 27. TOTAL SYNTHESIS OF OBTUSENOL

1982 ◽  
Vol 13 (13) ◽  
Author(s):  
A. G. GONZALEZ ◽  
J. D. MARTIN ◽  
C. PEREZ ◽  
M. A. RAMIREZ ◽  
F. RAVELO
Keyword(s):  
Natural Products ◽  
Total Synthesis ◽  
Marine Natural Products

scholarly journals Contiguous Quaternary Carbons: A Selection of Total Syntheses

Molecules ◽  
2020 ◽  
Vol 25 (17) ◽  
pp. 3841
Author(s):  
Alina Eggert ◽  
Christoph Etling ◽  
Dennis Lübken ◽  
Marius Saxarra ◽  
Markus Kalesse
Keyword(s):  
Natural Products ◽  
Total Synthesis ◽  
Status Quo ◽  
Total Syntheses ◽  
The Status ◽  
Selection Of ◽  
Quaternary Carbons

Contiguous quaternary carbons in terpene natural products remain a major challenge in total synthesis. Synthetic strategies to overcome this challenge will be a pivotal prerequisite to the medicinal application of natural products and their analogs or derivatives. In this review, we cover syntheses of natural products that exhibit a dense assembly of quaternary carbons and whose syntheses were uncompleted until recently. While discussing their syntheses, we not only cover the most recent total syntheses but also provide an update on the status quo of modern syntheses of complex natural products. Herein, we review (±)-canataxpropellane, (+)-waihoensene, (–)-illisimonin A and (±)-11-O-debenzoyltashironin as prominent examples of natural products bearing contiguous quaternary carbons.

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