TY - JOUR
T1 - Synthetic Studies of the Rubellin Natural Products
T2 - Development of a Stereoselective Strategy and Total Synthesis of (+)-Rubellin C
AU - Gartman, Jackson A.
AU - Tambar, Uttam K.
N1 - Funding Information:
Financial support was provided by W. W. Caruth, Jr., Endowed Scholarship, Welch Foundation (I-1748), the National Institutes of Health (R01GM102604), the American Chemical Society Petroleum Research Fund (59177-ND1), Teva Pharmaceuticals Marc A. Goshko Memorial Grant (60011-TEV), and the Sloan Research Fellowship. J.A.G. acknowledges the NIH Pharmacological Sciences Training Grant (GM007062) for funding. The authors thank Vincent Lynch (UT Austin) for X-ray crystal structural analysis, Hamid Baniasadi (UTSW) for high-resolution mass spectrometry assistance, and Jef De Brabander (UTSW), Joseph Ready (UTSW), Chuo Chen (UTSW), Tian Qin (UTSW), and Myles Smith (UTSW) for productive discussions. The authors also thank our diverse collection of lab members for creating an environment that supported the success of this project.
Publisher Copyright:
© 2021 American Chemical Society.
PY - 2021/8/20
Y1 - 2021/8/20
N2 - This manuscript describes our studies of the class of natural products known as the rubellins, culminating in the total synthesis of (+)-rubellin C. These anthraquinone-based natural products contain a variety of stereochemical and architectural motifs, including a 6-5-6-fused ring system, 5 stereogenic centers, and a central quaternary center. Herein, we report our development of a strategy to target the stereochemically dense core and anthraquinone nucleus, including approaches such as a bifunctional allylboron and vinyl triflate reagent, an anthraquinone benzylic metalation strategy, and a late-stage anthraquinone introduction strategy. Our studies culminate in a successful route to highly functionalized anthraquinone-based natural product scaffolds and a stereoselective total synthesis of (+)-rubellin C. These strategies and outcomes will aid in synthetic planning toward anthraquinone-based natural products of high interest.
AB - This manuscript describes our studies of the class of natural products known as the rubellins, culminating in the total synthesis of (+)-rubellin C. These anthraquinone-based natural products contain a variety of stereochemical and architectural motifs, including a 6-5-6-fused ring system, 5 stereogenic centers, and a central quaternary center. Herein, we report our development of a strategy to target the stereochemically dense core and anthraquinone nucleus, including approaches such as a bifunctional allylboron and vinyl triflate reagent, an anthraquinone benzylic metalation strategy, and a late-stage anthraquinone introduction strategy. Our studies culminate in a successful route to highly functionalized anthraquinone-based natural product scaffolds and a stereoselective total synthesis of (+)-rubellin C. These strategies and outcomes will aid in synthetic planning toward anthraquinone-based natural products of high interest.
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U2 - 10.1021/acs.joc.1c00920
DO - 10.1021/acs.joc.1c00920
M3 - Article
C2 - 34288689
AN - SCOPUS:85112384591
SN - 0022-3263
VL - 86
SP - 11237
EP - 11262
JO - Journal of Organic Chemistry
JF - Journal of Organic Chemistry
IS - 16
ER -