TY - JOUR

T1 - Contemporary Synthetic Strategies towards Secosteroids, abeo -Steroids, and Related Triterpenes

AU - Noack, Florian

AU - Heinze, Robert C.

AU - Heretsch, Philipp

N1 - Funding Information: Funding by Deutsche Forschungsgemeinschaft (DFG) is gratefully acknowledged (grants HE 7133/5-1 and HE 7133/7-1).DeutscheForschungsgemeinschaft(HE7133/5-1)DeutscheForschungsgemeinschaft(HE7133/7-1)

PY - 2019/5

Y1 - 2019/5

N2 - Steroids have long been sought after as synthetic targets. Their rearranged counterparts, though, have only recently received more attention, when isolation and biological testing programs revealed several molecular entities that were both structurally intriguing as well as biologically relevant. This review will highlight contemporary synthetic approaches towards the growing class of seco- and abeo -steroids and some related triterpenoid natural products. 1 Introduction 2 Cyclocitrinol 2.1 Li's Synthesis of Cyclocitrinol 2.2 Gui's Synthesis of Cyclocitrinol 3 Strophasterol 3.1 Heretsch's Synthesis of Strophasterol A 3.2 Kuwahara's Synthesis of Strophasterols A and B 4 Pleurocin A/Matsutakone and Pleurocin B 4.1 Heretsch's Synthesis of Pleurocin A/Matsutakone and Pleurocin B 5 Aplysiasecosterol A 5.1 Li's Synthesis of Aplysiasecosterol A 6 Glaucogenins C and D 6.1 Tian's Syntheses of 5,6-Dihydro-glaucogenin C and Glaucogenin D 7 Physalin B 7.1 Sodeoka's Synthesis of the DFGH Ring System of Physalin B 8 Limonin 8.1 Hirama's Synthesis of (±)-Limonin 9 Schiglautone A 9.1 Ding's Synthesis of (±)- atrop -Schiglautone A 10 Conclusion.

AB - Steroids have long been sought after as synthetic targets. Their rearranged counterparts, though, have only recently received more attention, when isolation and biological testing programs revealed several molecular entities that were both structurally intriguing as well as biologically relevant. This review will highlight contemporary synthetic approaches towards the growing class of seco- and abeo -steroids and some related triterpenoid natural products. 1 Introduction 2 Cyclocitrinol 2.1 Li's Synthesis of Cyclocitrinol 2.2 Gui's Synthesis of Cyclocitrinol 3 Strophasterol 3.1 Heretsch's Synthesis of Strophasterol A 3.2 Kuwahara's Synthesis of Strophasterols A and B 4 Pleurocin A/Matsutakone and Pleurocin B 4.1 Heretsch's Synthesis of Pleurocin A/Matsutakone and Pleurocin B 5 Aplysiasecosterol A 5.1 Li's Synthesis of Aplysiasecosterol A 6 Glaucogenins C and D 6.1 Tian's Syntheses of 5,6-Dihydro-glaucogenin C and Glaucogenin D 7 Physalin B 7.1 Sodeoka's Synthesis of the DFGH Ring System of Physalin B 8 Limonin 8.1 Hirama's Synthesis of (±)-Limonin 9 Schiglautone A 9.1 Ding's Synthesis of (±)- atrop -Schiglautone A 10 Conclusion.

KW - abeo

KW - -steroids

KW - biomimetic synthesis

KW - secosteroids

KW - semisynthesis

KW - total synthesis

KW - triterpenes

KW - abeo -steroids

UR - http://www.scopus.com/inward/record.url?scp=85065196401&partnerID=8YFLogxK

U2 - 10.1055/s-0037-1611576

DO - 10.1055/s-0037-1611576

M3 - Article

VL - 51

SP - 2039

EP - 2057

JO - SYNTHESIS-STUTTGART

JF - SYNTHESIS-STUTTGART

SN - 0039-7881

IS - 10

ER -