Total Synthesis of Natural Macrocyclic Diterpene (±)-Sinulariol-A

Abstract

Abstract: The total synthesis of natural macrocyclic diterpene (±)-Sinulariol-A(1), a marine cembraniol, starting from geranioLIs described.The key steps are the chromium-induced intramolecular cyclization of the ω-formyl-β-methoxycarbonylallyl halide 9, the phosphine-catalyzed Morita-Baylis-Hillman addition of methyl acrylate to aldehyde 5 and chlorination reaction of ester 7.The 14-membered ring cis-hydroxy ester 10was then underwent reduction with LiAlH₄to produce the title compound(±)-1 in 85% yield.

Key words: Cembrane-type macrocyclic diterpene, Natural product, Total synthesis, (±)-Sinulariol-A

CLC Number:

O621.3⁺4

TrendMD:

LI Shu-Hua, PENG Li-Zeng, ZHANG Tao, LI Yu-Lin . Total Synthesis of Natural Macrocyclic Diterpene (±)-Sinulariol-A[J]. Chem. J. Chinese Universities, 2003, 24(8): 1410.

[1]	HU Dongbao, ZHOU Beidou. Absolute Configuration Determination for Natural Products(Ⅱ)^†-Absolute Configuration Determination for Alkaloids by Comparing Computed Optical Rotations, ¹³C NMR and ¹H NMR with the Experimental Results [J]. Chem. J. Chinese Universities, 2016, 37(11): 1993.
[2]	HUANG Kang-Lun, XIE Long-Guan, LÜ Pei, GUO Cui, XU Xiao-Hua. Total Synthesis of Chelerythrine [J]. Chem. J. Chinese Universities, 2013, 34(8): 1858.
[3]	ZHANG Ying-Peng, ZHANG Wei-Na, YANG Yun-Shang, QIAO Ming. Total Synthesis of Natural Product Luxenchalcone [J]. Chem. J. Chinese Universities, 2013, 34(12): 2734.
[4]	HUANG Chu-Sheng, LIU Hong-Xing, SHI Jian-Cheng, LIN Sen, DUAN Hong-Xia. Total Syntheses of 5,7-Dihydroxy-3-isopentenylflavone and 5-Hydroxy-3-isopentenylflavone Natural Compounds [J]. Chem. J. Chinese Universities, 2012, 33(09): 1978.
[5]	ZHOU De-Jun, TOYOOKA Naoki. Syntheses of 5,8-Disubstituted Indolizidine Poison-frog Alkaloids [J]. Chem. J. Chinese Universities, 2012, 33(03): 511.
[6]	SHEN Lan, ZHAO Sheng-Ding, ZHU Hua-Jie*. Absolute Configuration Determination for Natural Products(Ⅰ)——Absolute Configuration Determination for Ketone, Lactone and Alcohol by Comparing Computed Optical Rotations and 13C NMR with the Experimental Results [J]. Chem. J. Chinese Universities, 2011, 32(11): 2568.
[7]	ZHANG Ying-Peng*, CHEN Yu-Tao, YANG Yun-Shang, GUAN Xiao. Modified Total Synthesis of Verbenachalcone [J]. Chem. J. Chinese Universities, 2010, 31(7): 1342.
[8]	XIA Ya-Mu, WANG Wei, YANG Feng-Ke, CHANG Liang. Total Synthesis of the Dilignan threo*-(±)-Diferuloysecoisolariciresinol [J]. Chem. J. Chinese Universities, 2010, 31(5): 947.
[9]	LIU Jun^1,2, NA Wan-Li³, XIN Wei-Hong³, LIU Li-Dan⁴, YU Bo¹, MA Tong-Hui¹, YANG Hong¹*. Natural Compound 20(S)-Protopanaxadiol Activates Cystic Fibrosis Transmembrane Conductance Regulator Chloride Channel [J]. Chem. J. Chinese Universities, 2008, 29(4): 731.
[10]	ZHANG Chen-Xi, BI Fu-Qiang, LI Yu-Lin^*. Total Synthesis of Ligudentatin A [J]. Chem. J. Chinese Universities, 2008, 29(11): 2191.
[11]	LI Yi¹, ZHANG Tao², LI Yu-Lin¹*. Total Synthesis of 6-Oxodendrolasinolide [J]. Chem. J. Chinese Universities, 2007, 28(7): 1292.
[12]	GUAN Yu-Kun^1,2*, FANG Li-Jing², TANG Zhi-Yong², LI Yu-Lin². Facile Total Synthesis of 3-Oxo-11,12,13-trihydroxyeudesm-4-ene [J]. Chem. J. Chinese Universities, 2007, 28(7): 1307.
[13]	GUAN Yu-Kun, LI Ping, ZHOU Gang, GAO Xiao-Lei, LI Yu-Lin. Total Synthesis of 5α-Hydroxy-isopterocarpolone [J]. Chem. J. Chinese Universities, 2005, 26(7): 1281.
[14]	SUN Bin, MEI Tian-Sheng, LIU Zuo-Sheng, LI Yu-Lin, LI Ying, PENG Li-Zeng . Asymmetric Synthesis of Natural Macrocyclic Diterpene(+)-Methyl Cembra-1,3,7,11-tetraene-16-carboxynate [J]. Chem. J. Chinese Universities, 2005, 26(5): 880.
[15]	WANG Jin-Jun, MORI Akiro, HATSUI Toshihide, TAKESHITA Hitoshi. Improvement of Total Synthesis of (±)-Hinesol and (±)-Agarospirol [J]. Chem. J. Chinese Universities, 2004, 25(6): 1051.

Total Synthesis of Natural Macrocyclic Diterpene (±)-Sinulariol-A

PDF (PC)

Knowledge

Abstract

Cite this article

share this article

References

Related Articles 15

Recommended Articles

Metrics

Comments