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Progress in Chemistry 2019, Vol. 31 Issue (11): 1460-1471 DOI: 10.7536/PC190809 Previous Articles   Next Articles

The Total Synthesis of ent-Kaurane Diterpenoids

Wu Li, Junjie Wang, Dawei Ma*()   

  1. Shanghai Institute of Organic Chemistry, Chinese Academy of Sciences, Shanghai 200032, China
  • Received: Online: Published:
  • Contact: Dawei Ma
  • About author:
    * E-mail:
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The ent-kaurane diterpenoids, widely distributed in terrestrial plants, represent an important group of tetracyclic diterpenes with diverse scaffolds and varied bioactivities. More and more studies have revealed that these compounds possess potent antitumor, antibacterial and anti-inflammatory activities. The tetracyclic ent-kaurane diterpenoids have attractive structural diversity owing to intramolecular cyclization, oxidative cleavage and rearrangements of their parent compounds. As a result, the total synthesis of ent-kaurane diterpenoids has received great attention from synthetic community during the past decades. This review describes the recent progress in this field, which includes total synthesis of C-20 non-oxygenated ent-kauranes such as(+)-lungshengenin D and pharicins A-C; total synthesis of C-20 oxygenated ent-kauranes such as maoecrystal P, eriocalyxin B, neolaxiflorin L and xerophilusin I; total synthesis of seco-ent-kauranes such as sculpomeatin N, trichorabdal A, maoecrystal Z, enmein, isodocarpin, sculponin R, londirabdiol, longirabdolactone and effusin; and total synthesis of nor or rearranged-ent-kauranes such as jungermannenones B and C, maoecrystal V, jungermatrobrunin A and kauradienone.

Key words: diterpenoids, ent-kaurane, total synthesis
Scheme. 1 Skelton of ent-Kaurene
Scheme. 2 Biosynthesis of ent-kaurene
Scheme. 3 Structures of some ent-kaurenes
Scheme. 4 The first asymmetric total synthesis of 1α,6α-diacetoxy-ent-kaura-9(11),16-dien-12,15-dione by Ma group
Scheme. 5 The first asymmetric total synthesis of lungshengenin D by Ma group
Scheme. 6 The first asymmetric total synthesis of pharicins A~C and(+)-7-O-acetylpharicin C by Ding group
Scheme. 7 Luo’s first total synthesis of maoecrystal P
Scheme. 8 The first total synthesis of(±)-eriocalyxin B,(±)-neolaxiflorin L and(±)-xerophilusin I by the Lee group
Scheme. 9 Biosynthesis of enmein type and spiro-lactone type diterpenoids
Scheme. 10 The first total synthesis of(±)-sculpomeatin N by the Zhai group
Scheme. 11 The total synthesis of(±)-sculpomeatin N by Thomson group
Scheme. 12 The total synthesis of(±)-trichorabdal A and(±)- maoecrystal Z by Liang group
Scheme. 13 The asymmetric total synthesis of(-)-enmein,(-)-isodocarpin and(-)-sculponin R by Dong group
Scheme. 14 The asymmetric total synthesis of(+)-londirabdiol,(-)-longirabdolactone and(-)-effusin by Li group
Scheme. 15 The total synthesis of(±)-jungermannenones B and(±)-jungermannenones C by Lei group
Scheme. 16 The asymmetric total synthesis of(-)-maoecrystal V by Baran group
Scheme. 17 Lei’s asymmetric total synthesis of(+)-jungermatrobrunin A
Scheme. 18 The asymmetric total synthesis of(+)-ent-kauradienone and(+)-jungermannenones C by the Lei group
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