ChemInform Abstract: Total Syntheses and Synthetic Studies of Spongiane Diterpenes

ChemInform ◽  
2008 ◽  
Vol 39 (22) ◽  
Author(s):  
Miguel A. Gonzalez
ChemInform ◽  
2010 ◽  
Vol 30 (44) ◽  
pp. no-no
Author(s):  
Hideharu Suzuki ◽  
Minoru Unemoto ◽  
Mayumi Hagiwara ◽  
Takako Ohyama ◽  
Yuusaku Yokoyama ◽  
...  

2019 ◽  
Vol 27 (12) ◽  
pp. 2449-2465 ◽  
Author(s):  
Kevin K.W. Kuan ◽  
Adrian W. Markwell-Heys ◽  
Michelle C. Cruickshank ◽  
Denise P. Tran ◽  
Robert M. Adlington ◽  
...  

2019 ◽  
Author(s):  
Cedric Hugelshofer ◽  
Vignesh Palani ◽  
Richmond Sarpong

The first total synthesis of the complex hexacylic Daphniphyllum alkaloid (–)-daphlongamine H in enantioenriched form has been accomplished. Key to the success of the strategy are a complexity-building Mannich reaction, efficient cyclizations, and a highly diastereoselective hydrogenation to assemble multigram quantities of the tricyclic core bearing four contiguous stereocenters. Following construction of the hydro-indene substructure by means of a Pauson–Khand reaction, endgame redox manipulations delivered the natural product. Importantly, the synthetic studies have also given access to (–)-isodaphlongamine H and led to a revision of the reported structure of deoxyisocalyciphylline B, which resulted in the proposal of a modified biosynthetic pathway to the calyciphylline B-type alkaloids.


1978 ◽  
Vol 9 (7) ◽  
Author(s):  
T. FUKUYAMA ◽  
F. NAKATSUBO ◽  
A. J. COCUZZA ◽  
Y. KISHI

2004 ◽  
Vol 339 (17) ◽  
pp. 2749-2759 ◽  
Author(s):  
Takeshi Yamamura ◽  
Noriyasu Hada ◽  
Asuka Kaburaki ◽  
Kimiaki Yamano ◽  
Tadahiro Takeda

2019 ◽  
Author(s):  
Cedric Hugelshofer ◽  
Vignesh Palani ◽  
Richmond Sarpong

The first total synthesis of the complex hexacylic Daphniphyllum alkaloid (–)-daphlongamine H in enantioenriched form has been accomplished. Key to the success of the strategy are a complexity-building Mannich reaction, efficient cyclizations, and a highly diastereoselective hydrogenation to assemble multigram quantities of the tricyclic core bearing four contiguous stereocenters. Following construction of the hydro-indene substructure by means of a Pauson–Khand reaction, endgame redox manipulations delivered the natural product. Importantly, the synthetic studies have also given access to (–)-isodaphlongamine H and led to a revision of the reported structure of deoxyisocalyciphylline B, which resulted in the proposal of a modified biosynthetic pathway to the calyciphylline B-type alkaloids.


2021 ◽  
Vol 68 (2) ◽  
pp. 247-267
Author(s):  
Jan Petrovčič ◽  
Chad Nicholas Ungarean ◽  
David Sarlah

Heterogeneity of meroterpenoids arising from their dual biosynthetic origins is constantly provoking synthetic chemists to utilize their ingenuity and revise their retrosynthetic logic. By studying recent publications on meroterpenoid synthesis,tremendous advances in the field of synthetic organic chemistry can be witnessed. This feature article covers some of the most intriguing total syntheses and synthetic studies towards the meroterpenoid class of natural products from the last five years.


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